# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_r100
_database_code_depnum_ccdc_archive 'CCDC 1980424'
loop_
_audit_author_name
_audit_author_address
Michael
;Universtiy of Regensburg
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.25
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      19
_cell_length_a                   7.94950(10)
_cell_length_b                   9.83780(10)
_cell_length_c                   15.6228(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1221.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10340
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.5080
_cell_measurement_theta_min      5.3050
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3604
_exptl_crystal_description       prism
_exptl_crystal_F_000             529.9915
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 3 0.0271
-5 1 -3 0.0528
1 -1 10 0.0528
2 2 -9 0.0300
-1 -1 -10 0.0506
1 -6 2 0.0854
0 -6 -5 0.0837
1 6 0 0.1175
0 -6 1 0.0969
-2 6 0 0.1014
1 2 9 0.0749
3 -1 8 0.0390
0 -3 -9 0.0653
-4 4 -1 0.0758
-5 2 1 0.0656
4 -3 -5 0.0596
-5 -2 3 0.0829

_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.092
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13755
_diffrn_reflns_theta_full        73.3723
_diffrn_reflns_theta_max         73.37
_diffrn_reflns_theta_min         5.31
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.9951
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00  36.00   1.00    1.00    --  -43.98   0.00-180.00  160
  2  ω    -49.00  28.00   1.00    1.00    --  -43.98  37.00   0.00   77
  3  ω     23.00  97.00   1.00    1.00    --   43.98-125.00  30.00   74
  4  ω     34.00  98.00   1.00    2.00    --  104.50 -45.00  60.00   64
  5  ω     31.00 118.00   1.00    2.00    --  104.50-125.00-150.00   87
  6  ω     78.00 174.00   1.00    2.00    --  104.50  61.00 150.00   96
  7  ω     21.00 110.00   1.00    2.00    --  104.50 -94.00   0.00   89
  8  ω     21.00 110.00   1.00    2.00    --  104.50 -94.00  90.00   89
  9  ω     32.00  91.00   1.00    2.00    --  104.50 -32.00  -9.00   59
 10  ω     30.00 136.00   1.00    2.00    --  104.50 -77.00-150.00  106
 11  ω     26.00 144.00   1.00    2.00    --  104.50 -15.00 120.00  118
 12  ω     31.00  91.00   1.00    2.00    --  104.50 -30.00-120.00   60
 13  ω   -118.00 -12.00   1.00    1.00    --  -43.98 -77.00 -90.00  106
 14  ω   -118.00 -12.00   1.00    1.00    --  -43.98 -77.00  30.00  106
 15  ω   -118.00 -12.00   1.00    1.00    --  -43.98 -77.00 150.00  106
 16  ω     78.00 174.00   1.00    2.00    --  104.50  61.00  30.00   96
 17  ω     78.00 174.00   1.00    2.00    --  104.50  61.00-150.00   96
 18  ω     78.00 178.00   1.00    2.00    --  104.50  30.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.988
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2391
_reflns_number_total             2441
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3623
_refine_diff_density_min         -0.2791
_refine_diff_density_rms         0.0443
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.08(14)
_refine_ls_d_res_high            0.8046
_refine_ls_d_res_low             8.3248
_refine_ls_goodness_of_fit_ref   1.0423
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.0423
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.2986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0864
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c)
;
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_refinement_flags_posn
O2 O 0.59681(13) 0.56159(11) 0.76505(7) 0.0227(2) Uani 1.000000 .
O5 O 0.09125(13) 0.47159(13) 0.63799(8) 0.0289(3) Uani 1.000000 .
O3 O 0.44696(13) 0.63080(10) 0.72863(7) 0.0221(2) Uani 1.000000 .
O1 O 0.48878(14) 0.46589(13) 0.89183(7) 0.0289(3) Uani 1.000000 .
O4 O 0.14294(16) 0.68762(12) 0.67752(9) 0.0328(3) Uani 1.000000 .
C12 C 0.18606(19) 0.57172(16) 0.66805(9) 0.0202(3) Uani 1.000000 .
C6 C 0.45162(17) 0.48284(14) 0.60440(9) 0.0169(3) Uani 1.000000 .
C5 C 0.36242(17) 0.51907(14) 0.68788(9) 0.0167(3) Uani 1.000000 .
C11 C 0.46744(19) 0.34996(16) 0.57488(10) 0.0220(3) Uani 1.000000 .
C7 C 0.51507(19) 0.58901(15) 0.55426(10) 0.0212(3) Uani 1.000000 .
C4 C 0.52923(19) 0.44316(15) 0.80601(10) 0.0203(3) Uani 1.000000 .
C3 C 0.36525(18) 0.40850(14) 0.75751(10) 0.0183(3) Uani 1.000000 .
C9 C 0.6117(2) 0.4299(2) 0.44840(11) 0.0286(4) Uani 1.000000 .
C8 C 0.5941(2) 0.56246(18) 0.47680(10) 0.0269(3) Uani 1.000000 .
C10 C 0.5483(2) 0.32447(18) 0.49742(11) 0.0273(3) Uani 1.000000 .
C2 C 0.2304(2) 0.41947(18) 0.82746(11) 0.0262(4) Uani 1.000000 .
C1 C 0.3135(2) 0.5037(2) 0.89606(12) 0.0330(4) Uani 1.000000 .
C13 C -0.0802(2) 0.5117(2) 0.61544(14) 0.0397(5) Uani 1.000000 .
H13a H -0.0768(2) 0.5768(13) 0.5697(7) 0.0595(7) Uiso 1.000000 GR
H13b H -0.1424(6) 0.4331(3) 0.5974(10) 0.0595(7) Uiso 1.000000 GR
H13c H -0.1339(7) 0.5516(15) 0.6644(3) 0.0595(7) Uiso 1.000000 GR
H4 H 0.620(3) 0.384(2) 0.8006(13) 0.028(5) Uiso 1.000000 .
H3 H 0.368(3) 0.318(2) 0.7317(13) 0.026(5) Uiso 1.000000 .
H9 H 0.667(3) 0.413(2) 0.3946(17) 0.039(6) Uiso 1.000000 .
H7 H 0.497(3) 0.684(2) 0.5747(13) 0.026(5) Uiso 1.000000 .
H10 H 0.556(3) 0.235(2) 0.4778(15) 0.041(6) Uiso 1.000000 .
H11 H 0.431(3) 0.275(2) 0.6067(14) 0.032(5) Uiso 1.000000 .
H2a H 0.203(3) 0.323(2) 0.8481(15) 0.038(6) Uiso 1.000000 .
H8 H 0.641(3) 0.644(2) 0.4437(14) 0.034(5) Uiso 1.000000 .
H2b H 0.123(3) 0.458(2) 0.8070(16) 0.044(6) Uiso 1.000000 .
H1a H 0.281(3) 0.479(2) 0.9549(14) 0.029(5) Uiso 1.000000 .
H1b H 0.301(4) 0.607(3) 0.8844(19) 0.058(8) Uiso 1.000000 .


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 1.4853(14) . ?
O2 C4 1.4337(18) . ?
O5 C12 1.3263(19) . ?
O5 C13 1.4620(18) . ?
O3 C5 1.4372(17) . ?
O1 C4 1.3968(19) . ?
O1 C1 1.444(2) . ?
O4 C12 1.200(2) . ?
C12 C5 1.5263(19) . ?
C6 C5 1.527(2) . ?
C6 C11 1.392(2) . ?
C6 C7 1.400(2) . ?
C5 C3 1.5386(19) . ?
C11 C10 1.393(2) . ?
C11 H11 0.94(2) . ?
C7 C8 1.388(2) . ?
C7 H7 1.00(2) . ?
C4 C3 1.5458(19) . ?
C4 H4 0.93(2) . ?
C3 C2 1.535(2) . ?
C3 H3 0.98(2) . ?
C9 C8 1.385(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.96(3) . ?
C8 H8 1.03(2) . ?
C10 H10 0.93(2) . ?
C2 C1 1.507(2) . ?
C2 H2a 1.03(2) . ?
C2 H2b 0.99(3) . ?
C1 H1a 0.98(2) . ?
C1 H1b 1.04(3) . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?

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
C4 O2 O3 104.06(10) . . ?
C13 O5 C12 114.48(13) . . ?
C5 O3 O2 101.19(9) . . ?
C1 O1 C4 107.90(12) . . ?
O4 C12 O5 125.95(14) . . ?
C5 C12 O5 109.99(12) . . ?
C5 C12 O4 124.05(14) . . ?
C11 C6 C5 122.98(13) . . ?
C7 C6 C5 118.12(13) . . ?
C7 C6 C11 118.87(14) . . ?
C12 C5 O3 105.06(11) . . ?
C6 C5 O3 109.87(11) . . ?
C6 C5 C12 109.42(11) . . ?
C3 C5 O3 102.75(11) . . ?
C3 C5 C12 113.38(12) . . ?
C3 C5 C6 115.61(12) . . ?
C10 C11 C6 119.91(15) . . ?
H11 C11 C6 122.3(13) . . ?
H11 C11 C10 117.7(13) . . ?
C8 C7 C6 120.70(15) . . ?
H7 C7 C6 117.7(12) . . ?
H7 C7 C8 121.5(12) . . ?
O1 C4 O2 112.62(12) . . ?
C3 C4 O2 106.05(11) . . ?
C3 C4 O1 108.16(12) . . ?
H4 C4 O2 99.9(13) . . ?
H4 C4 O1 111.5(13) . . ?
H4 C4 C3 118.4(13) . . ?
C4 C3 C5 101.71(11) . . ?
C2 C3 C5 116.33(12) . . ?
C2 C3 C4 102.98(12) . . ?
H3 C3 C5 110.6(12) . . ?
H3 C3 C4 112.8(12) . . ?
H3 C3 C2 111.8(12) . . ?
C10 C9 C8 119.45(15) . . ?
H9 C9 C8 119.2(14) . . ?
H9 C9 C10 121.3(14) . . ?
C9 C8 C7 120.13(15) . . ?
H8 C8 C7 117.1(13) . . ?
H8 C8 C9 122.8(12) . . ?
C9 C10 C11 120.92(16) . . ?
H10 C10 C11 119.1(15) . . ?
H10 C10 C9 119.9(15) . . ?
C1 C2 C3 103.82(13) . . ?
H2a C2 C3 107.9(13) . . ?
H2a C2 C1 112.3(13) . . ?
H2b C2 C3 113.6(14) . . ?
H2b C2 C1 113.5(14) . . ?
H2b C2 H2a 106(2) . . ?
C2 C1 O1 104.41(14) . . ?
H1a C1 O1 103.5(12) . . ?
H1a C1 C2 114.5(12) . . ?
H1b C1 O1 109.5(16) . . ?
H1b C1 C2 111.9(17) . . ?
H1b C1 H1a 112(2) . . ?
H13a C13 O5 109.5 . . ?
H13b C13 O5 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 O5 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_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
;
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_s105
_database_code_depnum_ccdc_archive 'CCDC 1980432'
loop_
_audit_author_name
_audit_author_address
Michael
;Universtiy of Regensburg
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RADNT01_s105                
;
PROBLEM: The radiation type should contain one of the following
RESPONSE: CuKa
;
# Added during the CSD deposition process: Tuesday 28 January 2020 03:59 PM
# end Validation Reply Form

_audit_creation_date             2019-07-25
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.07.11 svn.r3635 for OlexSys, GUI svn.r5848)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
simon.budde@ur.de
Birgit.Hischa@chemie.uni-regensburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O4'
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H16 O3'
_chemical_oxdiff_usercomment     Budde_Reiser_SBA403
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0160 0.0080 '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'
O O 0.0440 0.0270 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2541(3)
_cell_length_b                   6.14070(12)
_cell_length_c                   18.1087(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.293(2)
_cell_angle_gamma                90
_cell_volume                     1428.23(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7550
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      60.2480
_cell_measurement_theta_min      4.5430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
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            'clear dark colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 0 8 0.0668
9 0 -8 0.0606
-5 4 0 0.1250
3 0 -13 0.0738
5 -4 0 0.1073
0 2 -12 0.0932
-2 0 13 0.0661
-9 0 5 0.0697
4 4 -4 0.1210
-1 4 -2 0.1264
-1 -4 2 0.1037
3 0 11 0.0696
-4 0 -10 0.0741
1 -3 -10 0.1014
6 1 -12 0.0664
-8 0 -4 0.0772

_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.127
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
-9.0081 0.0056 7.9949 0.1579 0.8464 -0.5556
9.0081 -0.0056 -7.9949 -0.1579 -0.8464 0.5556
-5.0000 3.9977 -0.0111 -0.0752 -0.1449 -1.0430
3.0101 -0.0104 -12.9993 -0.8352 -0.5269 0.1727
5.0000 -3.9977 0.0111 0.0752 0.1449 1.0430
0.0092 1.9892 -12.0051 -0.8219 -0.5391 -0.3789
-2.0098 0.0106 13.0000 0.8850 0.4539 -0.1099
-9.0059 0.0031 4.9946 -0.0693 0.7754 -0.5593
4.0052 3.9954 -4.0057 0.0699 -0.8966 -0.4825
-0.9975 3.9965 -2.0087 -0.0275 -0.4842 -0.7941
-1.0030 -3.9967 2.0074 -0.0720 0.6302 0.6685
2.9929 0.0095 11.0031 0.9824 0.0415 0.2017
-3.9939 -0.0088 -10.0036 -0.9564 0.0552 -0.2633
1.0064 -3.0069 -9.9945 -0.8378 0.0726 0.5974
6.0105 0.9903 -11.9993 -0.5667 -0.8497 0.1801
-7.9993 -0.0042 -4.0056 -0.7011 0.4893 -0.5073

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        56.650
_diffrn_reflns_theta_max         59.969
_diffrn_reflns_theta_min         3.107
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1818
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -37.00   1.00    2.00    --    0.00 178.00 -30.00   49
  2  ω    -30.00  42.00   1.00    2.00    --    0.00  77.00-150.00   72
  3  ω   -142.00 -82.00   1.00   10.00    --  -70.50 -77.00 -60.00   60
  4  ω      0.00  48.00   1.00   10.00    --   75.56 -19.00 150.00   48
  5  ω      6.00  87.00   1.00   10.00    --   75.56 -57.00 -60.00   81
  6  ω     93.00 147.00   1.00   10.00    --   75.56 134.00-128.00   54
  7  ω      0.00  48.00   1.00   10.00    --   75.56 -19.00-180.00   48
  8  ω     52.00 145.00   1.00   10.00    --   75.56  57.00 150.00   93
  9  ω     97.00 147.00   1.00   10.00    --   75.56 125.00 -90.00   50
 10  ω     52.00 145.00   1.00   10.00    --   75.56  57.00  90.00   93
 11  ω      5.00  65.00   1.00   10.00    --   75.56 -38.00  30.00   60
 12  ω      5.00  65.00   1.00   10.00    --   75.56 -38.00-150.00   60
 13  ω     -5.00  76.00   1.00    2.00    --    0.00  19.00  30.00   81
 14  ω     -5.00  76.00   1.00    2.00    --    0.00  19.00 120.00   81
 15  ω   -141.00 -48.00   1.00   10.00    --  -70.50 -38.00 -30.00   93
 16  ω   -140.00 -46.00   1.00   10.00    --  -70.50 -57.00-120.00   94
 17  ω   -140.00 -92.00   1.00   10.00    --  -70.50 -57.00 -60.00   48
 18  ω     27.00 112.00   1.00   10.00    --   75.56-125.00-120.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0497043000
_diffrn_orient_matrix_UB_12      0.0435775000
_diffrn_orient_matrix_UB_13      0.0757225000
_diffrn_orient_matrix_UB_21      -0.0729793000
_diffrn_orient_matrix_UB_22      -0.1274537000
_diffrn_orient_matrix_UB_23      0.0237344000
_diffrn_orient_matrix_UB_31      0.0628152000
_diffrn_orient_matrix_UB_32      -0.1823207000
_diffrn_orient_matrix_UB_33      0.0014044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\b'
_diffrn_radiation_wavelength     1.39222
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2467
_reflns_number_total             2838
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.27
_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 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/3 (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.035
_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)+(0.0400P)²+0.5652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C10(H10), C9(H9), C18(H18), C11(H11), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.30379(7) 0.91595(14) 0.56968(5) 0.0242(2) Uani 1 1 d . . . . .
O4 O 0.39168(7) 0.95967(14) 0.53543(5) 0.0250(2) Uani 1 1 d . . . . .
O1 O 0.15609(7) 0.43313(16) 0.55119(5) 0.0312(2) Uani 1 1 d . . . . .
O2 O 0.14937(8) 0.74196(16) 0.61640(6) 0.0357(3) Uani 1 1 d . . . . .
C7 C 0.49958(10) 0.5446(2) 0.65309(7) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.52622(10) 0.7151(2) 0.61134(7) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.44382(10) 0.7508(2) 0.53867(7) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.472955 0.731905 0.494329 0.027 Uiso 1 1 calc R U . . .
C4 C 0.35912(10) 0.5759(2) 0.53891(7) 0.0222(3) Uani 1 1 d . . . . .
H4 H 0.351964 0.474635 0.496117 0.027 Uiso 1 1 calc R U . . .
C3 C 0.26205(10) 0.7205(2) 0.52967(7) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.18314(10) 0.6377(2) 0.57200(7) 0.0240(3) Uani 1 1 d . . . . .
C13 C 0.20394(9) 0.7744(2) 0.44750(7) 0.0226(3) Uani 1 1 d . . . . .
C14 C 0.15230(10) 0.9730(2) 0.43323(8) 0.0278(3) Uani 1 1 d . . . . .
H14 H 0.156660 1.071895 0.472789 0.033 Uiso 1 1 calc R U . . .
C12 C 0.61782(10) 0.8322(2) 0.63829(7) 0.0267(3) Uani 1 1 d . . . . .
H12 H 0.634935 0.947792 0.610489 0.032 Uiso 1 1 calc R U . . .
C10 C 0.65806(10) 0.5971(2) 0.74882(7) 0.0270(3) Uani 1 1 d . . . . .
H10 H 0.703487 0.556608 0.794590 0.032 Uiso 1 1 calc R U . . .
C8 C 0.39324(11) 0.4564(2) 0.61642(8) 0.0254(3) Uani 1 1 d . . . . .
C9 C 0.56628(10) 0.4831(2) 0.72210(7) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.549357 0.367036 0.749798 0.031 Uiso 1 1 calc R U . . .
C18 C 0.19823(10) 0.6301(2) 0.38769(8) 0.0296(3) Uani 1 1 d . . . . .
H18 H 0.232119 0.496460 0.396482 0.036 Uiso 1 1 calc R U . . .
C11 C 0.68294(10) 0.7722(2) 0.70769(7) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.744015 0.849771 0.726999 0.034 Uiso 1 1 calc R U . . .
C15 C 0.09443(11) 1.0249(2) 0.36066(8) 0.0320(3) Uani 1 1 d . . . . .
H15 H 0.058904 1.156719 0.351913 0.038 Uiso 1 1 calc R U . . .
C16 C 0.08951(10) 0.8804(3) 0.30111(8) 0.0323(3) Uani 1 1 d . . . . .
H16 H 0.051043 0.915230 0.252275 0.039 Uiso 1 1 calc R U . . .
C17 C 0.14191(11) 0.6848(3) 0.31459(8) 0.0343(3) Uani 1 1 d . . . . .
H17 H 0.139570 0.588686 0.274500 0.041 Uiso 1 1 calc R U . . .
C1 C 0.08398(12) 0.3317(3) 0.58938(9) 0.0388(4) Uani 1 1 d . . . . .
H1A H 0.073922 0.182022 0.574008 0.058 Uiso 1 1 calc R U . . .
H1B H 0.018444 0.406703 0.575864 0.058 Uiso 1 1 calc R U . . .
H1C H 0.111868 0.339225 0.643541 0.058 Uiso 1 1 calc R U . . .
H8A H 0.3464(11) 0.488(2) 0.6487(8) 0.024(4) Uiso 1 1 d . . . . .
H8B H 0.3915(12) 0.302(3) 0.6088(9) 0.034(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 O4 1.4733(12) . ?
O3 C3 1.4400(15) . ?
O4 C5 1.4512(15) . ?
O1 C2 1.3349(16) . ?
O1 C1 1.4512(16) . ?
O2 C2 1.1977(15) . ?
C7 C6 1.3874(18) . ?
C7 C8 1.5028(18) . ?
C7 C9 1.3930(18) . ?
C6 C5 1.5043(17) . ?
C6 C12 1.3916(18) . ?
C5 C4 1.5542(17) . ?
C4 C3 1.5378(17) . ?
C4 C8 1.5491(18) . ?
C3 C2 1.5284(17) . ?
C3 C13 1.5333(17) . ?
C13 C14 1.3911(19) . ?
C13 C18 1.3871(18) . ?
C14 C15 1.3854(19) . ?
C12 C11 1.3875(18) . ?
C10 C9 1.3834(19) . ?
C10 C11 1.3929(19) . ?
C18 C17 1.3909(19) . ?
C15 C16 1.386(2) . ?
C16 C17 1.379(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 O4 100.70(8) . . ?
C5 O4 O3 103.89(8) . . ?
C2 O1 C1 115.60(11) . . ?
C6 C7 C8 111.61(11) . . ?
C6 C7 C9 120.21(12) . . ?
C9 C7 C8 128.09(12) . . ?
C7 C6 C5 111.05(11) . . ?
C7 C6 C12 121.08(12) . . ?
C12 C6 C5 127.86(11) . . ?
O4 C5 C6 113.55(10) . . ?
O4 C5 C4 105.88(9) . . ?
C6 C5 C4 105.42(10) . . ?
C3 C4 C5 100.74(10) . . ?
C3 C4 C8 114.92(10) . . ?
C8 C4 C5 106.29(10) . . ?
O3 C3 C4 102.66(9) . . ?
O3 C3 C2 104.50(9) . . ?
O3 C3 C13 110.29(10) . . ?
C2 C3 C4 114.27(10) . . ?
C2 C3 C13 108.46(10) . . ?
C13 C3 C4 115.89(10) . . ?
O1 C2 C3 109.93(10) . . ?
O2 C2 O1 125.01(12) . . ?
O2 C2 C3 125.05(12) . . ?
C14 C13 C3 118.41(11) . . ?
C18 C13 C3 122.50(12) . . ?
C18 C13 C14 119.05(12) . . ?
C15 C14 C13 120.65(13) . . ?
C11 C12 C6 118.30(12) . . ?
C9 C10 C11 120.50(12) . . ?
C7 C8 C4 105.18(10) . . ?
C10 C9 C7 119.00(12) . . ?
C13 C18 C17 120.12(13) . . ?
C12 C11 C10 120.87(13) . . ?
C14 C15 C16 119.97(14) . . ?
C17 C16 C15 119.69(13) . . ?
C16 C17 C18 120.49(13) . . ?

_olex2_date_sample_data_collection 2019-07-23
_olex2_date_sample_submission    2019-07-18
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id SBA403
_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 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.789
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_s064
_database_code_depnum_ccdc_archive 'CCDC 1980425'
loop_
_audit_author_name
_audit_author_address
Michael
;Universtiy of Regensburg
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C52 H56 O20 '
_chemical_oxdiff_usercomment     Budde_Reiser_SBA373-minor
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4209(2)
_cell_length_b                   11.6353(2)
_cell_length_c                   12.1410(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.937(2)
_cell_angle_gamma                90
_cell_volume                     1143.85(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9476
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.9120
_cell_measurement_theta_min      5.3390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.21a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 6 1 0.0594
-2 3 7 0.0557
-1 -6 -4 0.0704
2 6 2 0.0587
3 -2 -7 0.0856
-4 -3 5 0.0591
-5 3 -1 0.0518
-2 6 -4 0.0846
5 -3 0 0.0440
-1 -6 5 0.0699
-2 -7 2 0.0674
5 1 -5 0.0871
3 -6 1 0.0426

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.101
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
2.5949 6.2258 1.2990 -0.5359 -0.5647 -0.6276
-2.1461 2.8682 7.2023 -0.6041 -0.6371 0.4786
-0.7462 -5.7719 -4.4840 0.6743 0.7107 0.2006
2.3831 6.2461 1.7385 -0.5612 -0.5914 -0.5791
2.6611 -2.0309 -7.3556 0.5498 0.5799 -0.6012
-4.2759 -3.2571 5.0882 -0.0317 -0.0338 0.9989
-4.5981 3.3659 -0.5026 0.6145 -0.7190 0.3247
-1.6294 5.7029 -3.7835 0.6060 -0.7094 -0.3597
4.9677 -2.6448 -0.2497 -0.5785 0.6768 -0.4552
-1.1111 -5.7394 5.1168 -0.4157 0.4868 0.7683
-1.7145 -7.0064 2.1996 0.0168 0.6497 0.7600
4.8276 0.9627 -5.3243 0.0091 0.3471 -0.9378
3.2303 -5.6669 0.9757 -0.4773 0.8787 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13754
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.165
_diffrn_reflns_theta_min         5.368
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  32.00   1.00    3.00    --  -42.29  37.00   0.00   99
  2  ω   -130.00  46.00   1.00    3.00    --  -42.29   0.00 -60.00  176
  3  ω     14.00 114.00   1.00    3.00    --   42.29  57.00 -90.00  100
  4  ω     35.00 116.00   1.00   12.00    --  111.00-111.00-180.00   81
  5  ω     35.00  69.00   1.00   12.00    --  111.00 -30.00   0.00   34
  6  ω     35.00  69.00   1.00   12.00    --  111.00 -30.00 120.00   34
  7  ω     82.00 158.00   1.00   12.00    --  111.00  61.00  60.00   76
  8  ω     28.00 109.00   1.00   12.00    --  111.00 -94.00 -90.00   81
  9  ω     82.00 158.00   1.00   12.00    --  111.00  61.00  30.00   76
 10  ω     85.00 158.00   1.00   12.00    --  111.00  45.00   0.00   73
 11  ω     28.00 109.00   1.00   12.00    --  111.00 -94.00 -30.00   81
 12  ω     35.00  69.00   1.00   12.00    --  111.00 -30.00  30.00   34
 13  ω     28.00 109.00   1.00   12.00    --  111.00 -94.00-150.00   81
 14  ω     38.00  77.00   1.00   12.00    --  111.00 -45.00-180.00   39
 15  ω     35.00  69.00   1.00   12.00    --  111.00 -30.00  60.00   34
 16  ω     78.00 158.00   1.00   12.00    --  111.00  77.00 -90.00   80
 17  ω     78.00 158.00   1.00   12.00    --  111.00  77.00  90.00   80
 18  ω     78.00 158.00   1.00   12.00    --  111.00  77.00 -60.00   80
 19  ω     35.00  69.00   1.00   12.00    --  111.00 -30.00-150.00   34
 20  ω     35.00  69.00   1.00   12.00    --  111.00 -30.00-120.00   34
 21  ω     82.00 158.00   1.00   12.00    --  111.00  61.00-120.00   76
 22  ω      2.00  98.00   1.00    3.00    --   42.29-125.00  90.00   96
 23  ω     10.00 118.00   1.00    3.00    --   42.29  77.00 150.00  108
 24  ω     10.00 118.00   1.00    3.00    --   42.29  77.00  60.00  108
 25  ω    -20.00  83.00   1.00    3.00    --   42.29 -99.00-180.00  103
 26  ω     10.00 118.00   1.00    3.00    --   42.29  77.00   0.00  108
 27  ω     38.00  77.00   1.00   12.00    --  111.00 -45.00 -30.00   39
 28  ω     85.00 158.00   1.00   12.00    --  111.00  45.00-180.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1269228000
_diffrn_orient_matrix_UB_12      -0.0084903000
_diffrn_orient_matrix_UB_13      -0.1183186000
_diffrn_orient_matrix_UB_21      0.0729877000
_diffrn_orient_matrix_UB_22      -0.1169177000
_diffrn_orient_matrix_UB_23      -0.0201522000
_diffrn_orient_matrix_UB_31      -0.1216402000
_diffrn_orient_matrix_UB_32      -0.0615287000
_diffrn_orient_matrix_UB_33      0.0547143000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2231
_reflns_number_total             2380
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_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     164
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.034
_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)+(0.0433P)²+0.5059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0856
_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 Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C5(H5), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.22116(10) 0.48778(7) 0.56495(7) 0.01888(18) Uani 1 1 d . . . . .
O2 O 0.37046(9) 0.49553(6) 0.78983(6) 0.01651(18) Uani 1 1 d . . . . .
O3 O 0.53428(10) 0.44938(7) 0.79079(7) 0.01907(19) Uani 1 1 d . . . . .
O4 O 0.70126(10) 0.55937(7) 0.94156(7) 0.02198(19) Uani 1 1 d . . . . .
O5 O 0.40362(11) 0.61620(8) 0.53527(7) 0.0263(2) Uani 1 1 d . . . . .
C1 C 0.33573(13) 0.56900(9) 0.59757(9) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.22010(13) 0.67022(9) 0.73911(9) 0.0153(2) Uani 1 1 d . . . . .
C10 C 0.56034(13) 0.73065(9) 0.87788(9) 0.0176(2) Uani 1 1 d . . . . .
H10A H 0.649009 0.785360 0.883070 0.021 Uiso 1 1 calc R . . . .
H10B H 0.459425 0.772152 0.875121 0.021 Uiso 1 1 calc R . . . .
C9 C 0.53812(13) 0.65259(9) 0.77347(9) 0.0152(2) Uani 1 1 d . . . . .
H9 H 0.577422 0.689343 0.713217 0.018 Uiso 1 1 calc R . . . .
C2 C 0.36488(13) 0.59923(9) 0.72532(9) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.16423(14) 0.76233(10) 0.66476(10) 0.0186(2) Uani 1 1 d . . . . .
H4 H 0.215818 0.779533 0.608163 0.022 Uiso 1 1 calc R . . . .
C12 C 0.64193(13) 0.54551(9) 0.82283(9) 0.0178(2) Uani 1 1 d . . . . .
H12 H 0.734774 0.538245 0.789204 0.021 Uiso 1 1 calc R . . . .
C8 C 0.14368(14) 0.64552(10) 0.82447(10) 0.0193(2) Uani 1 1 d . . . . .
H8 H 0.181069 0.584800 0.874708 0.023 Uiso 1 1 calc R . . . .
C5 C 0.03175(15) 0.82819(10) 0.67533(10) 0.0224(3) Uani 1 1 d . . . . .
H5 H -0.005460 0.889292 0.625548 0.027 Uiso 1 1 calc R . . . .
C11 C 0.60294(14) 0.64686(10) 0.97747(10) 0.0205(2) Uani 1 1 d . . . . .
H11A H 0.665822 0.684455 1.047117 0.025 Uiso 1 1 calc R . . . .
H11B H 0.503829 0.613854 0.990428 0.025 Uiso 1 1 calc R . . . .
C7 C 0.01080(14) 0.71230(11) 0.83423(10) 0.0234(3) Uani 1 1 d . . . . .
H7 H -0.040543 0.695669 0.891094 0.028 Uiso 1 1 calc R . . . .
C6 C -0.04559(14) 0.80321(11) 0.76007(11) 0.0240(3) Uani 1 1 d . . . . .
H6 H -0.134573 0.847232 0.766904 0.029 Uiso 1 1 calc R . . . .
C13 C 0.18424(15) 0.45514(11) 0.44530(10) 0.0231(3) Uani 1 1 d . . . . .
H13A H 0.144725 0.520973 0.398056 0.035 Uiso 1 1 calc GR . . . .
H13B H 0.101026 0.396368 0.429271 0.035 Uiso 1 1 calc GR . . . .
H13C H 0.282517 0.426474 0.429356 0.035 Uiso 1 1 calc GR . . . .


_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 C1 1.3308(14) . ?
O1 C13 1.4503(13) . ?
O2 O3 1.4774(10) . ?
O2 C2 1.4322(12) . ?
O3 C12 1.4249(13) . ?
O4 C12 1.3993(13) . ?
O4 C11 1.4526(14) . ?
O5 C1 1.1991(14) . ?
C1 C2 1.5429(14) . ?
C3 C2 1.5195(14) . ?
C3 C4 1.3970(15) . ?
C3 C8 1.3917(15) . ?
C10 C9 1.5286(14) . ?
C10 C11 1.5175(15) . ?
C9 C2 1.5450(14) . ?
C9 C12 1.5453(15) . ?
C4 C5 1.3882(16) . ?
C8 C7 1.3938(16) . ?
C5 C6 1.3910(18) . ?
C7 C6 1.3858(18) . ?

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 O1 C13 115.00(9) . . ?
C2 O2 O3 101.59(7) . . ?
C12 O3 O2 103.86(7) . . ?
C12 O4 C11 108.55(8) . . ?
O1 C1 C2 111.30(9) . . ?
O5 C1 O1 124.73(10) . . ?
O5 C1 C2 123.91(10) . . ?
C4 C3 C2 118.94(9) . . ?
C8 C3 C2 121.26(10) . . ?
C8 C3 C4 119.81(10) . . ?
C11 C10 C9 103.15(9) . . ?
C10 C9 C2 116.13(9) . . ?
C10 C9 C12 103.29(8) . . ?
C2 C9 C12 101.39(8) . . ?
O2 C2 C1 109.27(8) . . ?
O2 C2 C3 107.73(8) . . ?
O2 C2 C9 104.23(8) . . ?
C1 C2 C9 110.18(8) . . ?
C3 C2 C1 108.89(8) . . ?
C3 C2 C9 116.28(9) . . ?
C5 C4 C3 120.03(11) . . ?
O3 C12 C9 106.10(8) . . ?
O4 C12 O3 113.09(9) . . ?
O4 C12 C9 108.09(9) . . ?
C3 C8 C7 119.63(11) . . ?
C4 C5 C6 120.29(11) . . ?
O4 C11 C10 103.92(9) . . ?
C6 C7 C8 120.67(11) . . ?
C7 C6 C5 119.58(11) . . ?

_olex2_date_sample_data_collection 2019-04-18
_olex2_date_sample_submission    2019-04-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id 'SBA 373_minor'
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.594
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_s058
_database_code_depnum_ccdc_archive 'CCDC 1980428'
loop_
_audit_author_name
_audit_author_address
Michael
;Universtiy of Regensburg
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H17 N O7)'
_chemical_formula_sum            'C38 H34 N2 O14'
_chemical_formula_weight         742.67
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H17 N O7'
_chemical_oxdiff_usercomment     'Budde_Reiser_SBA 365'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.99870(10)
_cell_length_b                   12.21330(10)
_cell_length_c                   19.7453(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.0500(10)
_cell_angle_gamma                90
_cell_volume                     1687.49(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21787
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.2600
_cell_measurement_theta_min      4.1990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.21a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 7 0.0794
2 3 -11 0.0543
1 -3 -11 0.0696
4 1 -7 0.0502
0 -3 -12 0.0586
-4 -2 4 0.0705
2 4 10 0.0662
2 0 11 0.0764
-3 0 -10 0.0748
-2 1 12 0.0804
4 -2 -3 0.0692
2 -6 4 0.0754
-1 5 -9 0.0740
0 -2 12 0.0588
1 -6 8 0.0633
0 -7 -5 0.0799
-2 -7 5 0.0727

_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.128
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
-0.1224 6.7437 6.7260 0.2245 -0.7579 -0.6125
2.1696 2.5890 -10.5699 0.1353 -0.4555 0.8799
1.4001 -3.1722 -11.1294 -0.0758 0.2569 0.9635
3.7447 1.3649 -7.1163 0.5541 -0.2639 0.7895
-0.1260 -2.7465 -12.0043 -0.4108 0.1961 0.8904
-4.1220 -2.3290 4.0862 -0.7299 0.3478 -0.5885
1.6504 3.5771 10.3534 0.6762 -0.3226 -0.6623
2.3312 -0.1726 10.8704 0.8066 0.1496 -0.5719
-2.9224 0.4235 -9.6320 -0.8875 -0.1646 0.4304
-1.9254 1.2066 11.5415 -0.0313 -0.0060 -0.9995
4.3532 -1.5278 -2.9487 0.7869 0.1461 0.5995
2.1883 -6.4975 3.8614 0.5221 0.8524 0.0307
-1.0780 5.2143 -9.1065 -0.4646 -0.7585 0.4569
-0.4565 -2.2867 12.2268 0.2664 0.4348 -0.8602
1.3601 -5.6303 8.0956 0.4885 0.7975 -0.3541
-0.2249 -7.2506 -5.1219 -0.2494 0.8413 0.4797
-1.8204 -6.6276 4.9095 -0.2635 0.8890 -0.3746

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29386
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.375
_diffrn_reflns_theta_min         4.257
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -11.00   1.00    2.00    --  -42.81 -77.00-120.00  106
  2  ω   -113.00 -16.00   1.00    2.00    --  -42.81 -57.00 -60.00   97
  3  ω   -113.00 -16.00   1.00    2.00    --  -42.81 -57.00 120.00   97
  4  ω    -30.00  65.00   1.00    2.00    --   42.81 -37.00   0.00   95
  5  ω    -27.00  69.00   1.00    2.00    --   42.81 -57.00 -90.00   96
  6  ω    -27.00  69.00   1.00    2.00    --   42.81 -57.00-180.00   96
  7  ω     87.00 158.00   1.00    6.00    --  111.00  45.00 -30.00   71
  8  ω     87.00 158.00   1.00    6.00    --  111.00  45.00 120.00   71
  9  ω     73.00 158.00   1.00    6.00    --  111.00 125.00 -30.00   85
 10  ω     40.00  77.00   1.00    6.00    --  111.00 -45.00 -90.00   37
 11  ω     36.00  69.00   1.00    6.00    --  111.00 -30.00-150.00   33
 12  ω     39.00 121.00   1.00    6.00    --  111.00-125.00-150.00   82
 13  ω     39.00 121.00   1.00    6.00    --  111.00-125.00  60.00   82
 14  ω     36.00  69.00   1.00    6.00    --  111.00 -30.00-120.00   33
 15  ω     36.00  69.00   1.00    6.00    --  111.00 -30.00-180.00   33
 16  ω     30.00 109.00   1.00    6.00    --  111.00 -94.00 -60.00   79
 17  ω     37.00 142.00   1.00    6.00    --  111.00 -77.00 120.00  105
 18  ω     87.00 158.00   1.00    6.00    --  111.00  30.00  90.00   71
 19  ω     39.00 121.00   1.00    6.00    --  111.00-125.00  90.00   82
 20  ω     39.00 121.00   1.00    6.00    --  111.00-125.00 150.00   82
 21  ω     41.00 139.00   1.00    6.00    --  111.00 -61.00 -90.00   98
 22  ω     39.00 121.00   1.00    6.00    --  111.00-125.00 -90.00   82
 23  ω     36.00  69.00   1.00    6.00    --  111.00 -30.00   0.00   33
 24  ω     36.00  69.00   1.00    6.00    --  111.00 -30.00 -90.00   33
 25  ω     30.00 109.00   1.00    6.00    --  111.00 -94.00  90.00   79
 26  ω     87.00 158.00   1.00    6.00    --  111.00  30.00 150.00   71
 27  ω     41.00 131.00   1.00    6.00    --  111.00 -61.00 120.00   90
 28  ω     42.00  69.00   1.00    6.00    --  111.00-125.00 -30.00   27
 29  ω     48.00  83.00   1.00    6.00    --  111.00 -77.00 -90.00   35
 30  ω     43.00  69.00   1.00    6.00    --  111.00 -30.00 120.00   26
 31  ω     88.00 117.00   1.00    6.00    --  111.00  61.00-150.00   29
 32  ω     58.00 111.00   1.00    6.00    --  111.00-125.00 -60.00   53
 33  ω     87.00 121.00   1.00    6.00    --  111.00-125.00 -30.00   34
 34  ω     43.00  70.00   1.00    6.00    --  111.00 -15.00 150.00   27
 35  ω     83.00 110.00   1.00    6.00    --  111.00 -15.00 150.00   27
 36  ω     78.00 105.00   1.00    6.00    --  111.00 -77.00 -60.00   27
 37  ω     93.00 125.00   1.00    6.00    --  111.00 -77.00  60.00   32
 38  ω     45.00  76.00   1.00    6.00    --  111.00 -45.00  30.00   31
 39  ω     52.00 113.00   1.00    6.00    --  111.00 -15.00  30.00   61
 40  ω    117.00 154.00   1.00    6.00    --  111.00 -15.00  30.00   37
 41  ω     97.00 124.00   1.00    6.00    --  111.00  45.00 150.00   27
 42  ω     33.00  60.00   1.00    6.00    --  111.00 -94.00   0.00   27
 43  ω     78.00 109.00   1.00    6.00    --  111.00 -94.00  30.00   31
 44  ω    124.00 158.00   1.00    6.00    --  111.00 125.00   0.00   34
 45  ω     74.00 127.00   1.00    6.00    --  111.00 125.00 120.00   53
 46  ω     66.00 130.00   1.00    6.00    --  111.00 -61.00  60.00   64
 47  ω     59.00 141.00   1.00    6.00    --  111.00  14.00 -61.99   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2037595000
_diffrn_orient_matrix_UB_12      0.0064617000
_diffrn_orient_matrix_UB_13      0.0306021000
_diffrn_orient_matrix_UB_21      -0.0018982000
_diffrn_orient_matrix_UB_22      -0.1245776000
_diffrn_orient_matrix_UB_23      0.0121891000
_diffrn_orient_matrix_UB_31      0.0832149000
_diffrn_orient_matrix_UB_32      -0.0187509000
_diffrn_orient_matrix_UB_33      -0.0707572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6895
_reflns_number_total             7073
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 3211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7073
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0256
_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)+(0.0353P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0645
_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 Ternary CH refined with riding coordinates:
 C11(H11), C17(H17), C21(H21), C23(H23), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C26(H26), C28(H28), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.03568(19) 0.75997(10) 0.05547(6) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.37849(19) 0.54884(10) 0.59423(6) 0.0248(3) Uani 1 1 d . . . . .
O3 O 0.70190(17) 0.58137(10) 0.50235(6) 0.0216(2) Uani 1 1 d . . . . .
O4 O 0.83277(18) 0.30943(10) 0.46555(7) 0.0228(2) Uani 1 1 d . . . . .
O5 O 0.22759(17) 0.71333(10) 0.04538(6) 0.0222(2) Uani 1 1 d . . . . .
O6 O 0.51036(19) 0.63204(10) 0.49902(7) 0.0243(3) Uani 1 1 d . . . . .
O7 O 0.35581(18) 0.43532(10) 0.03572(6) 0.0242(3) Uani 1 1 d . . . . .
O8 O 0.96598(19) 0.44056(12) 0.53076(7) 0.0303(3) Uani 1 1 d . . . . .
O9 O -0.0975(2) 0.72555(11) -0.05214(6) 0.0268(3) Uani 1 1 d . . . . .
O10 O 0.4839(2) 0.58671(12) -0.00913(7) 0.0300(3) Uani 1 1 d . . . . .
O11 O 0.1192(2) 0.42073(13) 0.36197(7) 0.0337(3) Uani 1 1 d . . . . .
O12 O 0.1812(2) 0.59143(14) 0.38101(7) 0.0370(3) Uani 1 1 d . . . . .
O13 O 0.6872(3) 0.59563(16) 0.15376(7) 0.0461(4) Uani 1 1 d . . . . .
O14 O 0.6599(3) 0.41999(17) 0.14900(7) 0.0481(4) Uani 1 1 d . . . . .
N1 N 0.6680(2) 0.50669(17) 0.18047(8) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.1550(2) 0.51376(14) 0.34254(7) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.6576(2) 0.48677(14) 0.39381(8) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.6588(2) 0.50102(17) 0.25483(8) 0.0245(4) Uani 1 1 d . . . . .
C3 C 0.3650(2) 0.54125(14) 0.02352(8) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.7031(2) 0.58527(15) 0.36232(8) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.734371 0.646167 0.388546 0.026 Uiso 1 1 calc R . . . .
C5 C 0.8415(2) 0.40821(14) 0.49333(8) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.1256(2) 0.44936(14) 0.22486(9) 0.0210(3) Uani 1 1 d . . . . .
H6 H 0.092452 0.380386 0.240778 0.025 Uiso 1 1 calc R . . . .
C7 C 0.7023(2) 0.59334(16) 0.29204(9) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.730298 0.659228 0.270792 0.030 Uiso 1 1 calc R . . . .
C8 C 0.1849(2) 0.57405(14) 0.13236(8) 0.0187(3) Uani 1 1 d . . . . .
C9 C -0.0400(3) 0.66155(14) -0.16492(9) 0.0230(3) Uani 1 1 d . . . . .
C10 C 0.6682(2) 0.47732(13) 0.47120(8) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.4854(2) 0.45859(13) 0.62295(8) 0.0200(3) Uani 1 1 d . . . . .
H11 H 0.616953 0.481413 0.633266 0.024 Uiso 1 1 calc R . . . .
C12 C 0.2202(3) 0.63688(15) 0.24802(9) 0.0246(4) Uani 1 1 d . . . . .
H12 H 0.249401 0.691815 0.279137 0.029 Uiso 1 1 calc R . . . .
C13 C 0.1339(2) 0.47015(14) 0.15566(8) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.105422 0.414724 0.124801 0.024 Uiso 1 1 calc R . . . .
C14 C 0.0934(3) 0.66690(16) -0.21629(9) 0.0275(4) Uani 1 1 d . . . . .
H14 H 0.222941 0.670870 -0.205256 0.033 Uiso 1 1 calc R . . . .
C15 C 0.6064(2) 0.39599(15) 0.35429(9) 0.0219(3) Uani 1 1 d . . . . .
H15 H 0.570618 0.330982 0.375047 0.026 Uiso 1 1 calc R . . . .
C16 C 0.1949(2) 0.59913(13) 0.05654(8) 0.0185(3) Uani 1 1 d . . . . .
C17 C -0.0861(3) 0.69207(15) 0.01558(9) 0.0233(3) Uani 1 1 d . . . . .
H17 H -0.214052 0.690310 0.034868 0.028 Uiso 1 1 calc R . . . .
C18 C 0.2282(3) 0.65650(15) 0.17894(9) 0.0232(3) Uani 1 1 d . . . . .
H18 H 0.262751 0.725536 0.163521 0.028 Uiso 1 1 calc R . . . .
C19 C 0.1678(2) 0.53380(15) 0.26938(9) 0.0214(3) Uani 1 1 d . . . . .
C20 C 0.3886(3) 0.42303(14) 0.68690(8) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.4762(2) 0.43855(14) 0.50107(8) 0.0190(3) Uani 1 1 d . . . . .
H21 H 0.395629 0.402724 0.466522 0.023 Uiso 1 1 calc R . . . .
C22 C 0.5043(3) 0.36801(15) 0.00717(9) 0.0249(4) Uani 1 1 d . . . . .
H22A H 0.491933 0.368375 -0.041327 0.037 Uiso 1 1 calc GR . . . .
H22B H 0.492356 0.294356 0.023539 0.037 Uiso 1 1 calc GR . . . .
H22C H 0.627201 0.396651 0.020376 0.037 Uiso 1 1 calc GR . . . .
C23 C 0.0277(3) 0.65879(14) -0.09207(9) 0.0220(3) Uani 1 1 d . . . . .
H23 H 0.158558 0.687052 -0.088508 0.026 Uiso 1 1 calc R . . . .
C24 C 0.0034(2) 0.57630(14) 0.01780(8) 0.0203(3) Uani 1 1 d . . . . .
H24 H -0.076908 0.524313 0.042182 0.024 Uiso 1 1 calc R . . . .
C25 C 0.3886(3) 0.54878(14) 0.52356(9) 0.0219(3) Uani 1 1 d . . . . .
H25 H 0.260309 0.557138 0.503541 0.026 Uiso 1 1 calc R . . . .
C26 C -0.2916(3) 0.65658(17) -0.24995(10) 0.0320(4) Uani 1 1 d . . . . .
H26 H -0.421116 0.653433 -0.261172 0.038 Uiso 1 1 calc R . . . .
C27 C 0.4833(3) 0.37213(14) 0.56670(8) 0.0208(3) Uani 1 1 d . . . . .
H27A H 0.597613 0.327264 0.569153 0.025 Uiso 1 1 calc R . . . .
H27B H 0.372149 0.325137 0.569965 0.025 Uiso 1 1 calc R . . . .
C28 C 0.0342(3) 0.66634(17) -0.28420(10) 0.0321(4) Uani 1 1 d . . . . .
H28 H 0.124409 0.669108 -0.318178 0.038 Uiso 1 1 calc R . . . .
C29 C 0.0165(3) 0.54714(14) -0.05751(9) 0.0222(3) Uani 1 1 d . . . . .
H29A H 0.129658 0.503818 -0.066104 0.027 Uiso 1 1 calc R . . . .
H29B H -0.095557 0.506881 -0.072947 0.027 Uiso 1 1 calc R . . . .
C30 C 0.1919(3) 0.40640(16) 0.68669(10) 0.0289(4) Uani 1 1 d . . . . .
H30 H 0.120220 0.417082 0.647101 0.035 Uiso 1 1 calc R . . . .
C31 C -0.2333(3) 0.65614(16) -0.18215(10) 0.0290(4) Uani 1 1 d . . . . .
H31 H -0.323816 0.652214 -0.148335 0.035 Uiso 1 1 calc R . . . .
C32 C -0.1579(3) 0.66168(16) -0.30095(10) 0.0320(4) Uani 1 1 d . . . . .
H32 H -0.197618 0.661963 -0.346156 0.038 Uiso 1 1 calc R . . . .
C33 C 0.9950(3) 0.23907(15) 0.48025(9) 0.0258(4) Uani 1 1 d . . . . .
H33A H 0.982407 0.172444 0.454761 0.039 Uiso 1 1 calc GR . . . .
H33B H 0.999553 0.222368 0.527763 0.039 Uiso 1 1 calc GR . . . .
H33C H 1.110632 0.275780 0.467967 0.039 Uiso 1 1 calc GR . . . .
C34 C 0.6091(2) 0.40277(17) 0.28405(9) 0.0251(3) Uani 1 1 d . . . . .
H34 H 0.577945 0.342394 0.257348 0.030 Uiso 1 1 calc R . . . .
C35 C 0.2074(4) 0.35667(18) 0.80470(11) 0.0428(6) Uani 1 1 d . . . . .
H35 H 0.147215 0.334168 0.843921 0.051 Uiso 1 1 calc R . . . .
C36 C 0.4934(3) 0.40639(18) 0.74632(9) 0.0325(4) Uani 1 1 d . . . . .
H36 H 0.624927 0.417384 0.747069 0.039 Uiso 1 1 calc R . . . .
C37 C 0.1022(3) 0.37373(19) 0.74582(12) 0.0383(5) Uani 1 1 d . . . . .
H37 H -0.029443 0.363356 0.745605 0.046 Uiso 1 1 calc R . . . .
C38 C 0.4015(4) 0.3731(2) 0.80498(10) 0.0448(6) Uani 1 1 d . . . . .
H38 H 0.472394 0.362020 0.844677 0.054 Uiso 1 1 calc R . . . .


_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 O5 1.4758(17) . ?
O1 C17 1.418(2) . ?
O2 C11 1.442(2) . ?
O2 C25 1.399(2) . ?
O3 O6 1.4769(18) . ?
O3 C10 1.430(2) . ?
O4 C5 1.326(2) . ?
O4 C33 1.449(2) . ?
O5 C16 1.4311(19) . ?
O6 C25 1.418(2) . ?
O7 C3 1.318(2) . ?
O7 C22 1.448(2) . ?
O8 C5 1.199(2) . ?
O9 C17 1.399(2) . ?
O9 C23 1.442(2) . ?
O10 C3 1.198(2) . ?
O11 N2 1.227(2) . ?
O12 N2 1.227(2) . ?
O13 N1 1.216(3) . ?
O14 N1 1.228(3) . ?
N1 C2 1.472(2) . ?
N2 C19 1.469(2) . ?
C1 C4 1.394(2) . ?
C1 C10 1.533(2) . ?
C1 C15 1.399(2) . ?
C2 C7 1.377(3) . ?
C2 C34 1.379(3) . ?
C3 C16 1.540(2) . ?
C4 C7 1.391(2) . ?
C5 C10 1.535(2) . ?
C6 C13 1.392(2) . ?
C6 C19 1.384(2) . ?
C8 C13 1.398(2) . ?
C8 C16 1.531(2) . ?
C8 C18 1.393(2) . ?
C9 C14 1.393(3) . ?
C9 C23 1.507(2) . ?
C9 C31 1.390(3) . ?
C10 C21 1.552(2) . ?
C11 C20 1.508(2) . ?
C11 C27 1.532(2) . ?
C12 C18 1.387(3) . ?
C12 C19 1.379(3) . ?
C14 C28 1.396(3) . ?
C15 C34 1.390(2) . ?
C16 C24 1.556(2) . ?
C17 C24 1.547(2) . ?
C20 C30 1.392(3) . ?
C20 C36 1.387(3) . ?
C21 C25 1.547(2) . ?
C21 C27 1.529(2) . ?
C23 C29 1.527(2) . ?
C24 C29 1.533(2) . ?
C26 C31 1.392(3) . ?
C26 C32 1.389(3) . ?
C28 C32 1.380(3) . ?
C30 C37 1.394(3) . ?
C35 C37 1.381(4) . ?
C35 C38 1.373(4) . ?
C36 C38 1.396(3) . ?

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
C17 O1 O5 103.79(11) . . ?
C25 O2 C11 110.88(13) . . ?
C10 O3 O6 102.18(11) . . ?
C5 O4 C33 115.25(14) . . ?
C16 O5 O1 101.93(11) . . ?
C25 O6 O3 103.58(11) . . ?
C3 O7 C22 116.65(14) . . ?
C17 O9 C23 109.42(13) . . ?
O13 N1 O14 123.71(16) . . ?
O13 N1 C2 118.79(19) . . ?
O14 N1 C2 117.48(18) . . ?
O11 N2 O12 123.48(15) . . ?
O11 N2 C19 118.57(15) . . ?
O12 N2 C19 117.95(16) . . ?
C4 C1 C10 120.16(15) . . ?
C4 C1 C15 119.59(15) . . ?
C15 C1 C10 120.24(15) . . ?
C7 C2 N1 118.71(18) . . ?
C7 C2 C34 122.99(15) . . ?
C34 C2 N1 118.30(18) . . ?
O7 C3 C16 109.42(14) . . ?
O10 C3 O7 126.16(16) . . ?
O10 C3 C16 124.40(16) . . ?
C7 C4 C1 120.62(17) . . ?
O4 C5 C10 110.63(14) . . ?
O8 C5 O4 125.60(16) . . ?
O8 C5 C10 123.77(16) . . ?
C19 C6 C13 118.39(16) . . ?
C2 C7 C4 118.11(17) . . ?
C13 C8 C16 121.31(15) . . ?
C18 C8 C13 119.49(15) . . ?
C18 C8 C16 119.19(15) . . ?
C14 C9 C23 119.53(17) . . ?
C31 C9 C14 119.09(17) . . ?
C31 C9 C23 121.36(16) . . ?
O3 C10 C1 111.50(13) . . ?
O3 C10 C5 104.07(13) . . ?
O3 C10 C21 104.17(13) . . ?
C1 C10 C5 110.42(13) . . ?
C1 C10 C21 112.05(13) . . ?
C5 C10 C21 114.17(13) . . ?
O2 C11 C20 108.15(14) . . ?
O2 C11 C27 104.11(13) . . ?
C20 C11 C27 114.22(14) . . ?
C19 C12 C18 118.30(16) . . ?
C6 C13 C8 120.27(15) . . ?
C9 C14 C28 120.56(19) . . ?
C34 C15 C1 120.10(16) . . ?
O5 C16 C3 104.77(12) . . ?
O5 C16 C8 110.84(13) . . ?
O5 C16 C24 103.76(13) . . ?
C3 C16 C24 112.05(13) . . ?
C8 C16 C3 111.80(13) . . ?
C8 C16 C24 113.00(13) . . ?
O1 C17 C24 106.27(14) . . ?
O9 C17 O1 112.54(15) . . ?
O9 C17 C24 108.08(14) . . ?
C12 C18 C8 120.81(17) . . ?
C6 C19 N2 118.97(16) . . ?
C12 C19 N2 118.29(16) . . ?
C12 C19 C6 122.74(15) . . ?
C30 C20 C11 119.95(16) . . ?
C36 C20 C11 120.77(17) . . ?
C36 C20 C30 119.28(17) . . ?
C25 C21 C10 101.17(13) . . ?
C27 C21 C10 117.96(14) . . ?
C27 C21 C25 103.03(13) . . ?
O9 C23 C9 109.00(14) . . ?
O9 C23 C29 102.93(13) . . ?
C9 C23 C29 115.38(14) . . ?
C17 C24 C16 101.22(13) . . ?
C29 C24 C16 116.86(14) . . ?
C29 C24 C17 102.49(13) . . ?
O2 C25 O6 112.50(14) . . ?
O2 C25 C21 108.32(13) . . ?
O6 C25 C21 106.41(13) . . ?
C32 C26 C31 120.53(19) . . ?
C21 C27 C11 104.39(13) . . ?
C32 C28 C14 120.05(18) . . ?
C23 C29 C24 103.32(13) . . ?
C20 C30 C37 119.98(19) . . ?
C9 C31 C26 120.12(18) . . ?
C28 C32 C26 119.65(18) . . ?
C2 C34 C15 118.52(17) . . ?
C38 C35 C37 119.58(19) . . ?
C20 C36 C38 120.0(2) . . ?
C35 C37 C30 120.5(2) . . ?
C35 C38 C36 120.7(2) . . ?

_olex2_date_sample_data_collection 2019-04-08
_olex2_date_sample_submission    2019-03-27
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id 'SBA 365'
_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 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.893
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_S115
_database_code_depnum_ccdc_archive 'CCDC 1980429'
loop_
_audit_author_name
_audit_author_address
Michael
;Universtiy of Regensburg
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
loop_
_audit_author_email
simon.budde@ur.de
Birgit.Hischa@chemie.uni-regensburg.de
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.253
_chemical_oxdiff_formula         'C13 H14 O5'
_chemical_oxdiff_usercomment     'Budde_Reiser_SBA 389'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.4933(2)
_cell_length_b                   8.4381(2)
_cell_length_c                   15.4728(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.573(2)
_cell_angle_gamma                90
_cell_volume                     1228.64(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7040
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      74.0070
_cell_measurement_theta_min      4.6470
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       prism
_exptl_crystal_F_000             529.991
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 4 -2 0.0829
-1 5 3 0.0482
3 -4 -4 0.0601
4 -1 -7 0.0482
0 2 -9 0.0707
-2 -5 5 0.0705
1 0 10 0.0257
-5 -4 1 0.0594
-2 3 -7 0.0707
-5 0 -5 0.0362
-6 -2 3 0.0538
-6 1 0 0.0431
-3 4 -4 0.0684
-2 2 9 0.0165
2 -3 -9 0.0345
2 2 8 0.0230
4 0 6 0.0450
2 5 -1 0.0821

_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.059
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
3.9999 4.0000 -1.9997 -0.1469 -0.4390 -0.8681
-1.0001 4.9999 3.0001 0.7159 -0.3055 -0.5767
3.0000 -3.9999 -4.0000 -0.8848 0.1225 0.2940
4.0000 -0.9999 -6.9998 -0.8370 0.1363 -0.3401
-0.0000 2.0000 -9.0000 -0.1921 0.6346 -0.7142
-1.9999 -5.0000 4.9998 -0.0427 0.0144 1.0710
1.0000 -0.0000 10.0001 0.3147 -0.8987 0.4145
-4.9999 -4.0000 0.9996 0.2152 0.6302 0.8652
-2.0001 3.0000 -7.0001 0.2103 0.6661 -0.6885
-5.0000 -0.0000 -5.0003 0.3417 0.9560 -0.0145
-5.9999 -2.0001 2.9996 0.6021 0.5127 0.6968
-6.0000 0.9999 -0.0003 0.7609 0.6391 0.1056
-3.0001 4.0000 -4.0001 0.5443 0.5064 -0.6598
-2.0000 1.9999 9.0000 0.7957 -0.5552 0.1945
2.0000 -2.9999 -9.0000 -0.8912 0.5917 -0.0432
2.0000 2.0000 8.0002 0.3096 -0.9270 -0.0225
4.0000 0.0000 6.0003 -0.1883 -0.9220 0.1031
1.9999 5.0000 -0.9997 0.2130 -0.3289 -0.8881

_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.9900
_diffrn_reflns_Laue_measured_fraction_max 0.9900
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13027
_diffrn_reflns_point_group_measured_fraction_full 0.9900
_diffrn_reflns_point_group_measured_fraction_max 0.9900
_diffrn_reflns_theta_full        73.8355
_diffrn_reflns_theta_max         73.84
_diffrn_reflns_theta_min         4.70
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9900
_diffrn_measured_fraction_theta_max 0.9900
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -18.00   1.00    6.50    --  -42.41 -37.00 150.00   99
  2  ω    -98.00  -2.00   1.00    6.50    --  -42.41 125.00   0.00   96
  3  ω   -116.00 -14.00   1.00    6.50    --  -42.41 -57.00  90.00  102
  4  ω    -32.00  67.00   1.00    6.50    --   42.41 -37.00 -90.00   99
  5  ω      2.00  98.00   1.00    6.50    --   42.41-125.00 -90.00   96
  6  ω     33.00  77.00   1.00   26.00    --  106.40 -45.00   0.00   44
  7  ω     30.00  69.00   1.00   26.00    --  106.40 -30.00-150.00   39
  8  ω     78.00 158.00   1.00   26.00    --  106.40  30.00 -30.00   80
  9  ω     24.00 109.00   1.00   26.00    --  106.40 -94.00   0.00   85
 10  ω     30.00  69.00   1.00   26.00    --  106.40 -30.00  60.00   39
 11  ω     33.00  77.00   1.00   26.00    --  106.40 -45.00 150.00   44
 12  ω     33.00  77.00   1.00   26.00    --  106.40 -45.00 -30.00   44
 13  ω     74.00 158.00   1.00   26.00    --  106.40  77.00  90.00   84
 14  ω     33.00 121.00   1.00   26.00    --  106.40-125.00-180.00   88
 15  ω     30.00  69.00   1.00   26.00    --  106.40 -30.00-180.00   39
 16  ω     78.00 158.00   1.00   26.00    --  106.40  30.00  90.00   80
 17  ω     74.00 158.00   1.00   26.00    --  106.40  77.00 120.00   84
 18  ω     76.00 158.00   1.00   26.00    --  106.40  68.00 155.59   82
 19  ω     77.00 158.00   1.00   26.00    --  106.40  61.00-180.00   81
 20  ω     74.00 158.00   1.00   26.00    --  106.40  77.00-180.00   84
 21  ω   -117.00 -18.00   1.00    6.50    --  -42.41 -37.00 -30.00   99
 22  ω   -119.00 -10.00   1.00    6.50    --  -42.41 -77.00 -60.00  109
 23  ω   -119.00 -42.00   1.00    6.50    --  -42.41 -77.00  30.00   77
 24  ω     10.00 119.00   1.00    6.50    --   42.41  77.00-120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1109028000
_diffrn_orient_matrix_UB_12      0.0954600000
_diffrn_orient_matrix_UB_13      0.0425566000
_diffrn_orient_matrix_UB_21      -0.1125920000
_diffrn_orient_matrix_UB_22      -0.0364580000
_diffrn_orient_matrix_UB_23      -0.0786078000
_diffrn_orient_matrix_UB_31      -0.0428287000
_diffrn_orient_matrix_UB_32      -0.1513443000
_diffrn_orient_matrix_UB_33      0.0457272000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2283
_reflns_number_total             2463
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.3215
_refine_diff_density_min         -0.2185
_refine_diff_density_rms         0.0409
_refine_ls_d_res_high            0.8027
_refine_ls_d_res_low             9.4105
_refine_ls_goodness_of_fit_ref   1.0612
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.0612
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0808
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.10854(7) 0.20370(9) 0.71038(4) 0.02052(17) Uani 1.000000 .
O3 O 0.23500(8) 0.03070(8) 0.52578(5) 0.01900(17) Uani 1.000000 .
O2 O -0.00249(8) 0.05136(9) 0.60365(5) 0.02264(18) Uani 1.000000 .
O4 O 0.29954(8) -0.10828(9) 0.71644(5) 0.02504(18) Uani 1.000000 .
O5 O 0.52522(8) -0.07146(9) 0.69542(5) 0.02599(19) Uani 1.000000 .
C4 C 0.22168(10) 0.31762(12) 0.54638(6) 0.0179(2) Uani 1.000000 .
C10 C 0.36986(10) 0.13858(12) 0.65124(6) 0.0172(2) Uani 1.000000 .
C2 C 0.09985(10) 0.12700(11) 0.63495(6) 0.0171(2) Uani 1.000000 .
C11 C 0.38865(11) -0.02571(12) 0.69078(6) 0.0192(2) Uani 1.000000 .
C3 C 0.23149(10) 0.15189(12) 0.58815(6) 0.0165(2) Uani 1.000000 .
C12 C 0.50537(11) 0.16176(13) 0.60927(7) 0.0222(2) Uani 1.000000 .
C5 C 0.22077(13) 0.33395(14) 0.45715(7) 0.0253(2) Uani 1.000000 .
C9 C 0.21923(12) 0.45347(13) 0.59717(7) 0.0250(2) Uani 1.000000 .
C13 C 0.61035(11) 0.05710(14) 0.66566(8) 0.0258(2) Uani 1.000000 .
C1 C -0.01868(12) 0.20085(15) 0.75312(8) 0.0271(2) Uani 1.000000 .
C7 C 0.21231(12) 0.61780(13) 0.47013(8) 0.0266(2) Uani 1.000000 .
C8 C 0.21391(13) 0.60288(13) 0.55942(8) 0.0279(2) Uani 1.000000 .
C6 C 0.21673(14) 0.48418(15) 0.41947(8) 0.0303(3) Uani 1.000000 .
H10 H 0.3676(13) 0.2121(16) 0.6998(8) 0.022(3) Uiso 1.000000 .
H7 H 0.2087(15) 0.7217(18) 0.4434(9) 0.030(3) Uiso 1.000000 .
H1a H 0.0037(16) 0.263(2) 0.8063(10) 0.038(4) Uiso 1.000000 .
H12a H 0.4908(14) 0.1230(17) 0.5481(9) 0.027(3) Uiso 1.000000 .
H5 H 0.2232(15) 0.2421(19) 0.4226(9) 0.034(4) Uiso 1.000000 .
H1b H -0.0402(16) 0.095(2) 0.7688(10) 0.036(4) Uiso 1.000000 .
H1c H -0.0978(17) 0.243(2) 0.7144(10) 0.037(4) Uiso 1.000000 .
H12b H 0.5376(15) 0.2721(18) 0.6108(9) 0.029(3) Uiso 1.000000 .
H13a H 0.6812(16) 0.0055(18) 0.6353(10) 0.033(4) Uiso 1.000000 .
H9 H 0.2241(16) 0.4446(18) 0.6610(10) 0.035(4) Uiso 1.000000 .
H13b H 0.6532(15) 0.1144(17) 0.7190(9) 0.027(3) Uiso 1.000000 .
H3 H 0.152(2) 0.014(2) 0.5028(11) 0.041(4) Uiso 1.000000 .
H6 H 0.2188(17) 0.4918(19) 0.3570(11) 0.041(4) Uiso 1.000000 .
H8 H 0.2123(16) 0.6954(19) 0.5941(10) 0.036(4) Uiso 1.000000 .


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 C2 1.3276(12) . ?
O1 C1 1.4516(12) . ?
O3 C3 1.4095(11) . ?
O2 C2 1.2090(13) . ?
O4 C11 1.2030(13) . ?
O5 C11 1.3455(13) . ?
O5 C13 1.4628(13) . ?
C4 C3 1.5382(14) . ?
C4 C5 1.3865(14) . ?
C4 C9 1.3918(15) . ?
C10 C11 1.5163(14) . ?
C10 C3 1.5340(13) . ?
C10 C12 1.5281(13) . ?
C2 C3 1.5390(13) . ?
C12 C13 1.5183(15) . ?
C5 C6 1.3938(16) . ?
C9 C8 1.3876(16) . ?
C7 C8 1.3853(17) . ?
C7 C6 1.3770(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
C1 O1 C2 115.68(8) . . ?
C13 O5 C11 109.81(8) . . ?
C5 C4 C3 120.06(9) . . ?
C9 C4 C3 121.08(9) . . ?
C9 C4 C5 118.82(10) . . ?
C3 C10 C11 111.65(8) . . ?
C12 C10 C11 103.15(8) . . ?
C12 C10 C3 114.74(8) . . ?
O2 C2 O1 124.27(9) . . ?
C3 C2 O1 112.76(8) . . ?
C3 C2 O2 122.89(9) . . ?
O5 C11 O4 122.06(10) . . ?
C10 C11 O4 127.75(9) . . ?
C10 C11 O5 110.19(8) . . ?
C4 C3 O3 112.18(8) . . ?
C10 C3 O3 106.69(8) . . ?
C10 C3 C4 109.47(8) . . ?
C2 C3 O3 108.49(8) . . ?
C2 C3 C4 108.29(8) . . ?
C2 C3 C10 111.77(8) . . ?
C13 C12 C10 101.94(8) . . ?
C6 C5 C4 120.21(10) . . ?
C8 C9 C4 120.87(10) . . ?
C12 C13 O5 105.32(8) . . ?
C6 C7 C8 119.75(10) . . ?
C7 C8 C9 119.82(10) . . ?
C7 C6 C5 120.52(10) . . ?


_olex2_date_sample_data_collection 2019-08-28
_olex2_date_sample_submission    2019-08-27
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a Lindemann tube oil'
_olex2_submission_original_sample_id 'SBA 389'
_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 1.239
_oxdiff_exptl_absorpt_empirical_full_min 0.802
