# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_v070
_database_code_depnum_ccdc_archive 'CCDC 2331533'
loop_
_audit_author_name
_audit_author_address
'Ulmann Nadja'
;Institute of Physical and Theoretical Chemistry, University of Regensburg
Germany
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Nadja.Ulmann@chemie.uni-regensburg.de
?
Sabine.Stempfhuber@chemie.uni-regensburg.de
_chemical_name_common            'Vitamin B2'
_chemical_name_systematic        Riboflavin
_chemical_formula_moiety         'C17 H20 N4 O6'
_chemical_formula_sum            C~1~~7~H~2~~0~N~4~O~6~
_chemical_formula_weight         376.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H20 N4 O6'
_chemical_oxdiff_usercomment     Ulmann_Kunz_2
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           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.31333(5)
_cell_length_b                   15.11045(13)
_cell_length_c                   20.03449(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1608.51(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11360
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      74.8470
_cell_measurement_theta_min      2.9230
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
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            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 -1 0.0247
0 -10 1 0.0247
0 -1 -13 0.0178
3 1 0 0.1337
-3 1 0 0.1454
0 -10 -3 0.0244
0 0 13 0.0133
-3 3 -8 0.1063
0 8 -8 0.0177
0 9 5 0.0166
0 -9 6 0.0228

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
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
-0.1476 9.7565 -1.2228 -0.1680 0.9040 -0.3932
0.1476 -9.7565 1.2228 0.1680 -0.9040 0.3932
0.0109 -1.3690 -12.8794 0.9760 0.1825 0.1187
3.4194 1.2428 0.3319 -0.2271 0.4279 0.8748
-3.4419 0.5794 0.1539 0.1434 -0.2755 -0.9505
-0.0951 -9.6136 -2.5632 0.4523 -0.8238 0.3416
0.0477 0.2046 13.0024 -0.9563 -0.2860 -0.0606
-3.0007 2.9938 -8.0052 0.6512 0.1800 -0.8792
-0.0001 7.9943 -8.0015 0.3669 0.9185 -0.2541
-0.0010 9.0032 4.9944 -0.6083 0.7013 -0.3574
0.0003 -8.9957 6.0025 -0.1939 -0.9622 0.3012

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16921
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.054
_diffrn_reflns_theta_min         3.664
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      '123.01(10) K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_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     72.00 103.00   0.50    0.95    --   66.00  73.00 110.69   62
  2  ω     90.00 127.00   0.50    0.95    --   79.75  36.00 155.82   74
  3  ω     89.00 127.00   0.50    0.95    --   79.75  35.00 102.83   76
  4  ω     78.00 124.00   0.50    0.95    --   75.87  28.00  18.00   92
  5  ω     39.00 113.00   0.50    0.95    --   75.87   0.00-120.00  148
  6  ω     45.00 118.00   0.50    0.95    --   79.75   5.00  16.07  146
  7  ω     42.00  73.00   0.50    0.95    --   79.75 -70.00  84.38   62
  8  ω     30.00 104.00   0.50    0.95    --   63.22-146.00  -7.00  148
  9  ω     38.00  84.00   0.50    0.95    --   75.87 -95.00 -60.00   92
 10  ω     38.00  84.00   0.50    0.95    --   75.87 -95.00  51.00   92
 11  ω     25.00  72.00   0.50    0.95    --   63.22 -95.00  51.00   94
 12  ω     38.00  84.00   0.50    0.95    --   75.87 -95.00 150.00   92
 13  ω   -103.00 -34.00   0.50    0.95    --  -78.25 118.00 158.72  138
 14  ω   -120.00 -73.00   0.50    0.95    --  -76.58-126.00 159.00   94
 15  ω   -120.00 -73.00   0.50    0.95    --  -76.58-125.00-120.00   94
 16  ω   -115.00 -34.00   0.50    0.95    --  -73.72 146.00  43.00  162
 17  ω   -121.00 -39.00   0.50    0.95    --  -78.25 149.00  86.43  164
 18  ω   -115.00 -84.00   0.50    0.95    --  -78.25 -72.00  48.25   62
 19  ω   -125.00 -90.00   0.50    0.95    --  -78.25 -38.00  73.28   70
 20  ω   -117.00 -86.00   0.50    0.95    --  -78.25 -68.00  67.93   62
 21  ω   -115.00 -81.00   0.50    0.95    --  -70.00 -47.00 -15.31   68
 22  ω   -120.00 -88.00   0.50    0.95    --  -78.25 -59.00-160.81   64
 23  ω   -111.00 -65.00   0.50    0.95    --  -63.51 -28.00-142.00   92
 24  ω   -124.00 -78.00   0.50    0.95    --  -76.58 -28.00-142.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494818000
_diffrn_orient_matrix_UB_12      -0.0271129000
_diffrn_orient_matrix_UB_13      -0.0729403000
_diffrn_orient_matrix_UB_21      0.0943260000
_diffrn_orient_matrix_UB_22      0.0911005000
_diffrn_orient_matrix_UB_23      -0.0237773000
_diffrn_orient_matrix_UB_31      0.2697380000
_diffrn_orient_matrix_UB_32      -0.0368540000
_diffrn_orient_matrix_UB_33      -0.0050679000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3105
_reflns_number_total             3236
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.037
_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)+(0.0557P)²+0.2795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(2)
 0.2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
O3 \\sim O1A \\sim O1: within 1.7A with sigma of 0.005 and sigma for terminal
atoms of 0.005 within 1.7A
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C14(H14)
5.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O4 O 0.6079(3) 0.57572(9) 0.60206(7) 0.0184(3) Uani 1 1 d . . . . .
O6 O 1.2784(3) 0.60980(10) 0.49012(7) 0.0202(3) Uani 1 1 d . . . . .
O2 O 1.3984(3) 0.88437(10) 0.76568(7) 0.0226(3) Uani 1 1 d . . . . .
O5 O 1.0762(3) 0.74891(9) 0.57068(7) 0.0197(3) Uani 1 1 d . . . . .
O3 O 0.4133(3) 0.72698(11) 0.67250(7) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.347596 0.680806 0.688050 0.035 Uiso 1 1 calc R U . . .
O1 O 0.893(9) 0.930(3) 0.939(2) 0.028(4) Uani 0.25(9) 1 d . U P A 1
N1 N 0.7216(3) 0.69980(11) 0.78564(8) 0.0168(4) Uani 1 1 d . . . . .
N4 N 1.0559(3) 0.79597(11) 0.77107(8) 0.0186(4) Uani 1 1 d . . . . .
N3 N 1.1227(4) 0.91336(11) 0.84929(9) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.5906(3) 0.78672(11) 0.90419(8) 0.0180(4) Uani 1 1 d . . . . .
C12 C 0.8595(4) 0.77088(13) 0.80646(10) 0.0167(4) Uani 1 1 d . . . . .
C9 C 0.7771(4) 0.81320(13) 0.86749(10) 0.0177(4) Uani 1 1 d . . . . .
C15 C 0.7070(4) 0.66325(13) 0.59642(10) 0.0160(4) Uani 1 1 d . . . . .
C11 C 1.2002(4) 0.86447(13) 0.79367(10) 0.0192(4) Uani 1 1 d . . . . .
C1 C 0.5224(4) 0.66803(13) 0.82385(9) 0.0171(4) Uani 1 1 d . . . . .
C10 C 0.9159(4) 0.89437(14) 0.88814(10) 0.0211(4) Uani 1 1 d . . . . .
C13 C 0.7891(4) 0.65922(13) 0.72078(10) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.3839(4) 0.59193(14) 0.80728(10) 0.0200(4) Uani 1 1 d . . . . .
C5 C 0.2621(4) 0.68280(14) 0.92400(10) 0.0187(4) Uani 1 1 d . . . . .
C4 C 0.1265(4) 0.60870(13) 0.90782(10) 0.0195(4) Uani 1 1 d . . . . .
C14 C 0.6757(4) 0.71293(13) 0.66287(10) 0.0171(4) Uani 1 1 d . . . . .
H14 H 0.762860 0.771453 0.659890 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1934(4) 0.56170(13) 0.84852(10) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.4618(4) 0.71354(13) 0.88388(10) 0.0179(4) Uani 1 1 d . . . . .
C17 C 1.0153(4) 0.61816(14) 0.50529(10) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.9821(4) 0.66001(13) 0.57398(10) 0.0164(4) Uani 1 1 d . . . . .
C8 C -0.0828(4) 0.57620(14) 0.95192(11) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.0582(5) 0.47783(14) 0.83060(11) 0.0256(5) Uani 1 1 d . . . . .
H17A H 0.948(4) 0.5600(16) 0.5020(11) 0.011(5) Uiso 1 1 d . . . . .
H17B H 0.935(5) 0.6539(16) 0.4699(12) 0.019(6) Uiso 1 1 d . . . . .
H13A H 0.721(5) 0.5974(17) 0.7200(11) 0.018(6) Uiso 1 1 d . . . . .
H5A H 0.230(5) 0.7120(18) 0.9621(13) 0.020(6) Uiso 1 1 d . . . . .
H7A H 0.137(6) 0.452(2) 0.7921(15) 0.037(8) Uiso 1 1 d . . . . .
H6 H 1.340(6) 0.660(2) 0.4765(16) 0.041(9) Uiso 1 1 d . . . . .
H16 H 1.072(5) 0.6301(15) 0.6040(12) 0.014(6) Uiso 1 1 d . . . . .
H8A H -0.243(6) 0.570(2) 0.9279(14) 0.033(8) Uiso 1 1 d . . . . .
H8B H -0.116(6) 0.615(2) 0.9876(15) 0.037(8) Uiso 1 1 d . . . . .
H2 H 0.423(5) 0.5581(16) 0.7656(12) 0.019(6) Uiso 1 1 d . . . . .
H13B H 0.978(6) 0.6606(18) 0.7191(12) 0.025(6) Uiso 1 1 d . . . . .
H5 H 1.189(7) 0.747(2) 0.6053(18) 0.051(10) Uiso 1 1 d . . . . .
H3A H 1.216(6) 0.955(2) 0.8626(14) 0.030(7) Uiso 1 1 d . . . . .
H15 H 0.613(4) 0.6962(15) 0.5633(11) 0.012(5) Uiso 1 1 d . . . . .
H8C H -0.046(6) 0.518(2) 0.9730(14) 0.036(8) Uiso 1 1 d . . . . .
H7B H 0.073(6) 0.436(2) 0.8680(15) 0.036(8) Uiso 1 1 d . . . . .
H7C H -0.121(8) 0.489(2) 0.8252(17) 0.050(9) Uiso 1 1 d . . . . .
H4 H 0.502(6) 0.572(2) 0.5777(15) 0.031(8) Uiso 1 1 d . . . . .
O1A O 0.843(4) 0.9426(13) 0.9339(8) 0.027(2) Uani 0.75(9) 1 d . U P A 2


_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
O4 C15 1.428(2) . ?
O4 H4 0.75(3) . ?
O6 C17 1.436(3) . ?
O6 H6 0.87(3) . ?
O2 C11 1.230(3) . ?
O5 C16 1.435(2) . ?
O5 H5 0.92(4) . ?
O3 H3 0.8400 . ?
O3 C14 1.423(3) . ?
O1 C10 1.16(4) . ?
N1 C12 1.366(3) . ?
N1 C1 1.392(3) . ?
N1 C13 1.481(2) . ?
N4 C12 1.317(3) . ?
N4 C11 1.365(3) . ?
N3 C11 1.399(3) . ?
N3 C10 1.377(3) . ?
N3 H3A 0.85(3) . ?
N2 C9 1.297(3) . ?
N2 C6 1.363(3) . ?
C12 C9 1.448(3) . ?
C9 C10 1.490(3) . ?
C15 C14 1.537(3) . ?
C15 C16 1.530(3) . ?
C15 H15 0.97(2) . ?
C1 C2 1.405(3) . ?
C1 C6 1.422(3) . ?
C10 O1A 1.234(16) . ?
C13 C14 1.539(3) . ?
C13 H13A 1.00(3) . ?
C13 H13B 1.01(3) . ?
C2 C3 1.384(3) . ?
C2 H2 1.00(2) . ?
C5 C4 1.370(3) . ?
C5 C6 1.410(3) . ?
C5 H5A 0.90(3) . ?
C4 C3 1.429(3) . ?
C4 C8 1.503(3) . ?
C14 H14 1.0000 . ?
C3 C7 1.500(3) . ?
C17 C16 1.525(3) . ?
C17 H17A 0.95(2) . ?
C17 H17B 0.99(3) . ?
C16 H16 0.89(3) . ?
C8 H8A 0.99(3) . ?
C8 H8B 0.95(3) . ?
C8 H8C 0.99(3) . ?
C7 H7A 0.96(3) . ?
C7 H7B 0.99(3) . ?
C7 H7C 0.98(4) . ?

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
C15 O4 H4 107(2) . . ?
C17 O6 H6 111(2) . . ?
C16 O5 H5 99(2) . . ?
C14 O3 H3 109.5 . . ?
C12 N1 C1 120.76(16) . . ?
C12 N1 C13 117.62(17) . . ?
C1 N1 C13 121.61(17) . . ?
C12 N4 C11 118.97(17) . . ?
C11 N3 H3A 118(2) . . ?
C10 N3 C11 125.10(18) . . ?
C10 N3 H3A 116(2) . . ?
C9 N2 C6 117.70(17) . . ?
N1 C12 C9 116.30(18) . . ?
N4 C12 N1 119.15(17) . . ?
N4 C12 C9 124.55(19) . . ?
N2 C9 C12 125.00(19) . . ?
N2 C9 C10 118.35(18) . . ?
C12 C9 C10 116.64(18) . . ?
O4 C15 C14 110.10(15) . . ?
O4 C15 C16 110.25(16) . . ?
O4 C15 H15 109.8(14) . . ?
C14 C15 H15 106.6(13) . . ?
C16 C15 C14 111.93(16) . . ?
C16 C15 H15 108.1(14) . . ?
O2 C11 N4 120.96(19) . . ?
O2 C11 N3 119.1(2) . . ?
N4 C11 N3 119.97(19) . . ?
N1 C1 C2 123.41(18) . . ?
N1 C1 C6 118.06(18) . . ?
C2 C1 C6 118.50(19) . . ?
O1 C10 N3 119(2) . . ?
O1 C10 C9 125(2) . . ?
N3 C10 C9 114.19(17) . . ?
O1A C10 N3 123.2(6) . . ?
O1A C10 C9 122.5(6) . . ?
N1 C13 C14 110.38(17) . . ?
N1 C13 H13A 108.2(14) . . ?
N1 C13 H13B 105.2(15) . . ?
C14 C13 H13A 109.8(14) . . ?
C14 C13 H13B 110.8(15) . . ?
H13A C13 H13B 112(2) . . ?
C1 C2 H2 120.4(15) . . ?
C3 C2 C1 120.80(18) . . ?
C3 C2 H2 118.8(15) . . ?
C4 C5 C6 122.01(19) . . ?
C4 C5 H5A 120.2(18) . . ?
C6 C5 H5A 117.7(18) . . ?
C5 C4 C3 118.16(19) . . ?
C5 C4 C8 121.14(19) . . ?
C3 C4 C8 120.69(19) . . ?
O3 C14 C15 107.23(16) . . ?
O3 C14 C13 111.11(17) . . ?
O3 C14 H14 109.3 . . ?
C15 C14 C13 110.66(16) . . ?
C15 C14 H14 109.3 . . ?
C13 C14 H14 109.3 . . ?
C2 C3 C4 120.94(19) . . ?
C2 C3 C7 119.08(19) . . ?
C4 C3 C7 120.0(2) . . ?
N2 C6 C1 122.09(19) . . ?
N2 C6 C5 118.38(18) . . ?
C5 C6 C1 119.54(19) . . ?
O6 C17 C16 109.88(16) . . ?
O6 C17 H17A 105.7(14) . . ?
O6 C17 H17B 108.5(16) . . ?
C16 C17 H17A 113.7(13) . . ?
C16 C17 H17B 111.8(15) . . ?
H17A C17 H17B 107(2) . . ?
O5 C16 C15 108.45(15) . . ?
O5 C16 C17 107.85(15) . . ?
O5 C16 H16 108.6(15) . . ?
C15 C16 H16 109.4(15) . . ?
C17 C16 C15 112.88(16) . . ?
C17 C16 H16 109.6(15) . . ?
C4 C8 H8A 112.8(17) . . ?
C4 C8 H8B 112(2) . . ?
C4 C8 H8C 113.2(19) . . ?
H8A C8 H8B 106(2) . . ?
H8A C8 H8C 107(3) . . ?
H8B C8 H8C 106(2) . . ?
C3 C7 H7A 109.1(19) . . ?
C3 C7 H7B 109.0(17) . . ?
C3 C7 H7C 110(2) . . ?
H7A C7 H7B 108(2) . . ?
H7A C7 H7C 114(3) . . ?
H7B C7 H7C 106(3) . . ?

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
O4 C15 C14 O3 -68.0(2) . . . . ?
O4 C15 C14 C13 53.3(2) . . . . ?
O4 C15 C16 O5 -178.47(15) . . . . ?
O4 C15 C16 C17 62.1(2) . . . . ?
O6 C17 C16 O5 65.5(2) . . . . ?
O6 C17 C16 C15 -174.68(16) . . . . ?
N1 C12 C9 N2 2.6(3) . . . . ?
N1 C12 C9 C10 -176.04(18) . . . . ?
N1 C1 C2 C3 177.67(19) . . . . ?
N1 C1 C6 N2 0.6(3) . . . . ?
N1 C1 C6 C5 -179.61(17) . . . . ?
N1 C13 C14 O3 -51.6(2) . . . . ?
N1 C13 C14 C15 -170.59(17) . . . . ?
N4 C12 C9 N2 -176.88(19) . . . . ?
N4 C12 C9 C10 4.5(3) . . . . ?
N2 C9 C10 O1 11(3) . . . . ?
N2 C9 C10 N3 175.07(19) . . . . ?
N2 C9 C10 O1A -8.6(15) . . . . ?
C12 N1 C1 C2 -175.80(18) . . . . ?
C12 N1 C1 C6 2.1(3) . . . . ?
C12 N1 C13 C14 -80.6(2) . . . . ?
C12 N4 C11 O2 172.90(18) . . . . ?
C12 N4 C11 N3 -7.3(3) . . . . ?
C12 C9 C10 O1 -171(3) . . . . ?
C12 C9 C10 N3 -6.2(3) . . . . ?
C12 C9 C10 O1A 170.1(15) . . . . ?
C9 N2 C6 C1 -1.6(3) . . . . ?
C9 N2 C6 C5 178.65(18) . . . . ?
C11 N4 C12 N1 -177.01(17) . . . . ?
C11 N4 C12 C9 2.5(3) . . . . ?
C11 N3 C10 O1 167(3) . . . . ?
C11 N3 C10 C9 1.7(3) . . . . ?
C11 N3 C10 O1A -174.5(15) . . . . ?
C1 N1 C12 N4 176.01(17) . . . . ?
C1 N1 C12 C9 -3.5(3) . . . . ?
C1 N1 C13 C14 98.4(2) . . . . ?
C1 C2 C3 C4 2.2(3) . . . . ?
C1 C2 C3 C7 -177.19(19) . . . . ?
C10 N3 C11 O2 -174.96(19) . . . . ?
C10 N3 C11 N4 5.3(3) . . . . ?
C13 N1 C12 N4 -5.0(3) . . . . ?
C13 N1 C12 C9 175.49(18) . . . . ?
C13 N1 C1 C2 5.3(3) . . . . ?
C13 N1 C1 C6 -176.86(17) . . . . ?
C2 C1 C6 N2 178.58(18) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C5 C4 C3 C2 -2.3(3) . . . . ?
C5 C4 C3 C7 177.09(19) . . . . ?
C4 C5 C6 N2 -178.67(19) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C14 C15 C16 O5 -55.6(2) . . . . ?
C14 C15 C16 C17 -174.99(16) . . . . ?
C6 N2 C9 C12 -0.1(3) . . . . ?
C6 N2 C9 C10 178.55(18) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
C6 C5 C4 C8 178.93(19) . . . . ?
C16 C15 C14 O3 168.99(16) . . . . ?
C16 C15 C14 C13 -69.7(2) . . . . ?
C8 C4 C3 C2 179.19(19) . . . . ?
C8 C4 C3 C7 -1.4(3) . . . . ?

_olex2_date_sample_data_collection 2022-06-30
_olex2_date_sample_submission    2022-06-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder inert oil'
_olex2_submission_original_sample_id 
'3,4-Dimethoxycinnamic acid / Riboflavin /ACN'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.436
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(2)
2 0.2(2)

_exptl_crystal_recrystallization_method 'Precipiation from solvent'
_chemical_properties_physical    
Air-sensitive,Oxygen-sensitive,Light-sensitive,Photo-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_v069
_database_code_depnum_ccdc_archive 'CCDC 2331534'
loop_
_audit_author_name
_audit_author_address
'Ulmann Nadja'
;Institute of Physical and Theoretical Chemistry, University of Regensburg
Germany
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Nadja.Ulmann@chemie.uni-regensburg.de
?
Sabine.Stempfhuber@chemie.uni-regensburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 N4 O6'
_chemical_formula_sum            'C17 H20 N4 O6'
_chemical_formula_weight         376.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H20 N4 O6'
_chemical_oxdiff_usercomment     Ulmann_Kunz_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.30940(10)
_cell_length_b                   15.11770(10)
_cell_length_c                   20.0373(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1608.31(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8634
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.7730
_cell_measurement_theta_min      3.6450
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 0 0.0053
0 -10 0 0.0133
3 0 -1 0.1085
0 3 -12 0.0060
0 -3 12 0.0140
-3 7 1 0.0739

_exptl_crystal_size_max          0.22
_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
0.0414 9.8154 0.0849 -0.0806 -0.0107 0.9967
-0.0414 -9.8154 -0.0849 0.0806 0.0107 -0.9967
3.4316 -0.3851 -1.0321 -0.9910 -0.0788 -0.1086
0.0055 3.1915 -12.3011 -0.0228 -0.9512 0.3078
-0.0055 -3.1915 12.3011 0.0228 0.9512 -0.3078
-3.0000 7.0000 1.0000 0.8197 0.0647 0.7722

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14730
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.975
_diffrn_reflns_theta_min         3.663
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  87.00   0.50    5.00    --   63.22-126.00 141.00  106
  2  ω    -88.00 -28.00   0.50    5.00    --  -63.51  -5.00 -69.00  120
  3  ω     49.00  75.00   0.50    5.00    --   75.87-132.00-124.00   52
  4  ω     67.00 100.00   0.50    5.00    --   75.87   5.00 106.00   66
  5  ω   -100.00 -75.00   0.50    5.00    --  -76.58 145.00  25.00   50
  6  ω     36.00 107.00   0.50    5.00    --   63.22  15.00 -60.00  142
  7  ω     30.00  57.00   0.50    5.00    --   63.22 -95.00-150.00   54
  8  ω    -92.00 -66.00   0.50    5.00    --  -63.51 125.00 150.00   52
  9  ω     55.00  81.00   0.50    5.00    --   75.80 -95.00 -60.00   52
 10  ω   -120.00 -95.00   0.50    5.00    --  -76.58-125.00 -90.00   50
 11  ω    -66.00 -37.00   0.50    5.00    --  -76.58 125.00  30.00   58
 12  ω    -97.00 -37.00   0.50    5.00    --  -78.25 116.00  95.46  120
 13  ω    -69.00 -44.00   0.50    5.00    --  -78.25 119.00 167.29   50
 14  ω   -112.00 -87.00   0.50    5.00    --  -78.25 -90.00-148.99   50
 15  ω   -103.00 -78.00   0.50    5.00    --  -78.25 117.00-137.82   50
 16  ω    -74.00 -39.00   0.50    5.00    --  -78.25 107.00-114.49   70
 17  ω    -85.00 -35.00   0.50    5.00    --  -78.25 122.00 -27.80  100
 18  ω   -101.00 -73.00   0.50    5.00    --  -78.25 117.00  56.76   56
 19  ω   -103.00 -69.00   0.50    5.00    --  -78.25 119.00-160.54   68
 20  ω   -104.00 -74.00   0.50    5.00    --  -78.25 119.00 167.29   60
 21  ω    -74.00 -35.00   0.50    5.00    --  -78.25 118.00  16.16   78
 22  ω     51.00 105.00   0.50    5.00    --   79.75-118.00-161.69  108
 23  ω     65.00 119.00   0.50    5.00    --   79.75  22.00 173.83  108
 24  ω     67.00 107.00   0.50    5.00    --   79.75  20.00-113.04   80
 25  ω     67.00  92.00   0.50    5.00    --   79.75-122.00  90.37   50
 26  ω     84.00 122.00   0.50    5.00    --   79.75  13.00 126.07   76
 27  ω     52.00  79.00   0.50    5.00    --   79.75  13.00 126.07   54
 28  ω     91.00 117.00   0.50    5.00    --   79.75  23.00 -85.02   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2895842000
_diffrn_orient_matrix_UB_12      -0.0069934000
_diffrn_orient_matrix_UB_13      -0.0000942000
_diffrn_orient_matrix_UB_21      -0.0000304000
_diffrn_orient_matrix_UB_22      -0.0017513000
_diffrn_orient_matrix_UB_23      0.0768706000
_diffrn_orient_matrix_UB_31      -0.0198554000
_diffrn_orient_matrix_UB_32      0.1016149000
_diffrn_orient_matrix_UB_33      0.0013335000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3077
_reflns_number_total             3253
_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 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.22(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.037
_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)+(0.0415P)²+0.2160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O4 O 0.6068(3) 0.57567(8) 0.60208(7) 0.0150(3) Uani 1 1 d . . . . .
O6 O 1.2776(3) 0.60977(9) 0.49002(7) 0.0165(3) Uani 1 1 d . . . . .
O2 O 1.3988(3) 0.88448(9) 0.76579(7) 0.0186(3) Uani 1 1 d . . . . .
O5 O 1.0763(3) 0.74875(8) 0.57070(7) 0.0156(3) Uani 1 1 d . . . . .
O3 O 0.4120(3) 0.72641(9) 0.67251(7) 0.0198(3) Uani 1 1 d . . . . .
O1 O 0.8528(3) 0.94018(10) 0.93485(8) 0.0302(4) Uani 1 1 d . . . . .
N1 N 0.7218(3) 0.69978(10) 0.78564(7) 0.0137(3) Uani 1 1 d . . . . .
N4 N 1.0558(3) 0.79609(10) 0.77108(8) 0.0150(3) Uani 1 1 d . . . . .
N3 N 1.1231(3) 0.91345(10) 0.84927(8) 0.0162(3) Uani 1 1 d . . . . .
N2 N 0.5908(3) 0.78690(9) 0.90420(8) 0.0142(3) Uani 1 1 d . . . . .
C12 C 0.8597(4) 0.77097(11) 0.80660(9) 0.0133(4) Uani 1 1 d . . . . .
C9 C 0.7775(4) 0.81335(12) 0.86737(9) 0.0145(4) Uani 1 1 d . . . . .
C15 C 0.7075(3) 0.66319(11) 0.59651(9) 0.0124(3) Uani 1 1 d . . . . .
C13 C 0.7893(4) 0.65950(12) 0.72074(9) 0.0139(4) Uani 1 1 d . . . . .
C11 C 1.1999(4) 0.86457(12) 0.79370(9) 0.0157(4) Uani 1 1 d . . . . .
C1 C 0.5226(4) 0.66809(11) 0.82389(9) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.3837(4) 0.59204(12) 0.80747(9) 0.0159(4) Uani 1 1 d . . . . .
C4 C 0.1269(4) 0.60870(12) 0.90776(9) 0.0156(4) Uani 1 1 d . . . . .
C10 C 0.9160(4) 0.89452(12) 0.88818(9) 0.0172(4) Uani 1 1 d . . . . .
C6 C 0.4620(4) 0.71353(11) 0.88372(9) 0.0143(4) Uani 1 1 d . . . . .
C14 C 0.6760(4) 0.71256(12) 0.66289(9) 0.0136(4) Uani 1 1 d . . . . .
C3 C 0.1933(4) 0.56178(12) 0.84859(10) 0.0163(4) Uani 1 1 d . . . . .
C5 C 0.2620(4) 0.68280(12) 0.92400(9) 0.0153(4) Uani 1 1 d . . . . .
C17 C 1.0153(3) 0.61809(12) 0.50536(9) 0.0143(4) Uani 1 1 d . . . . .
C16 C 0.9816(3) 0.65991(11) 0.57394(9) 0.0129(3) Uani 1 1 d . . . . .
C8 C -0.0830(4) 0.57605(13) 0.95196(10) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.0585(4) 0.47778(12) 0.83046(10) 0.0215(4) Uani 1 1 d . . . . .
H17A H 0.936(5) 0.6552(14) 0.4717(12) 0.021(6) Uiso 1 1 d . . . . .
H5A H 0.230(4) 0.7174(14) 0.9646(12) 0.012(5) Uiso 1 1 d . . . . .
H15 H 0.614(4) 0.6960(14) 0.5646(10) 0.013(5) Uiso 1 1 d . . . . .
H17B H 0.950(4) 0.5579(13) 0.5028(10) 0.006(5) Uiso 1 1 d . . . . .
H13A H 0.727(5) 0.5980(16) 0.7202(11) 0.020(6) Uiso 1 1 d . . . . .
H13B H 0.974(5) 0.6610(14) 0.7183(11) 0.014(5) Uiso 1 1 d . . . . .
H14 H 0.765(5) 0.7710(15) 0.6599(11) 0.018(6) Uiso 1 1 d . . . . .
H8A H -0.111(5) 0.6135(16) 0.9887(13) 0.029(6) Uiso 1 1 d . . . . .
H16 H 1.080(4) 0.6236(13) 0.6077(11) 0.018(5) Uiso 1 1 d . . . . .
H2 H 0.425(4) 0.5610(13) 0.7664(11) 0.014(5) Uiso 1 1 d . . . . .
H6 H 1.336(5) 0.6584(17) 0.4776(13) 0.028(7) Uiso 1 1 d . . . . .
H8B H -0.239(5) 0.5660(15) 0.9280(13) 0.027(6) Uiso 1 1 d . . . . .
H3A H 1.220(5) 0.9597(18) 0.8631(13) 0.033(7) Uiso 1 1 d . . . . .
H8C H -0.045(5) 0.5191(16) 0.9738(13) 0.029(6) Uiso 1 1 d . . . . .
H3 H 0.400(6) 0.7654(17) 0.7030(15) 0.038(8) Uiso 1 1 d . . . . .
H7A H 0.141(5) 0.4485(15) 0.7898(13) 0.027(6) Uiso 1 1 d . . . . .
H7B H -0.123(6) 0.4889(17) 0.8224(13) 0.032(7) Uiso 1 1 d . . . . .
H7C H 0.080(5) 0.4333(17) 0.8691(14) 0.041(8) Uiso 1 1 d . . . . .
H5 H 1.192(6) 0.7515(18) 0.6042(16) 0.044(8) Uiso 1 1 d . . . . .
H4 H 0.496(6) 0.5699(17) 0.5728(14) 0.037(8) 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
O4 C15 1.431(2) . ?
O4 H4 0.84(3) . ?
O6 C17 1.432(2) . ?
O6 H6 0.84(3) . ?
O2 C11 1.232(2) . ?
O5 C16 1.436(2) . ?
O5 H5 0.91(3) . ?
O3 C14 1.430(2) . ?
O3 H3 0.85(3) . ?
O1 C10 1.210(2) . ?
N1 C12 1.368(2) . ?
N1 C13 1.480(2) . ?
N1 C1 1.391(2) . ?
N4 C12 1.317(2) . ?
N4 C11 1.365(2) . ?
N3 C11 1.397(2) . ?
N3 C10 1.378(3) . ?
N3 H3A 0.91(3) . ?
N2 C9 1.299(2) . ?
N2 C6 1.366(2) . ?
C12 C9 1.444(2) . ?
C9 C10 1.490(3) . ?
C15 C14 1.534(2) . ?
C15 C16 1.525(2) . ?
C15 H15 0.95(2) . ?
C13 C14 1.533(3) . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.98(2) . ?
C1 C2 1.405(3) . ?
C1 C6 1.419(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.97(2) . ?
C4 C3 1.426(3) . ?
C4 C5 1.369(3) . ?
C4 C8 1.507(3) . ?
C6 C5 1.412(3) . ?
C14 H14 1.00(2) . ?
C3 C7 1.502(3) . ?
C5 H5A 0.98(2) . ?
C17 C16 1.523(2) . ?
C17 H17A 0.97(2) . ?
C17 H17B 0.98(2) . ?
C16 H16 1.01(2) . ?
C8 H8A 0.94(3) . ?
C8 H8B 0.97(3) . ?
C8 H8C 0.99(2) . ?
C7 H7A 1.03(3) . ?
C7 H7B 0.99(3) . ?
C7 H7C 1.03(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
C15 O4 H4 107.7(18) . . ?
C17 O6 H6 110.4(19) . . ?
C16 O5 H5 104.2(18) . . ?
C14 O3 H3 106(2) . . ?
C12 N1 C13 117.65(16) . . ?
C12 N1 C1 120.58(15) . . ?
C1 N1 C13 121.76(16) . . ?
C12 N4 C11 118.83(16) . . ?
C11 N3 H3A 118.8(18) . . ?
C10 N3 C11 125.02(16) . . ?
C10 N3 H3A 116.0(17) . . ?
C9 N2 C6 117.47(16) . . ?
N1 C12 C9 116.51(16) . . ?
N4 C12 N1 118.95(16) . . ?
N4 C12 C9 124.54(17) . . ?
N2 C9 C12 124.99(17) . . ?
N2 C9 C10 118.11(16) . . ?
C12 C9 C10 116.89(17) . . ?
O4 C15 C14 109.95(14) . . ?
O4 C15 C16 110.47(14) . . ?
O4 C15 H15 109.9(13) . . ?
C14 C15 H15 105.8(12) . . ?
C16 C15 C14 112.15(15) . . ?
C16 C15 H15 108.4(13) . . ?
N1 C13 C14 110.75(15) . . ?
N1 C13 H13A 108.5(14) . . ?
N1 C13 H13B 106.1(13) . . ?
C14 C13 H13A 110.7(14) . . ?
C14 C13 H13B 109.9(13) . . ?
H13A C13 H13B 111(2) . . ?
O2 C11 N4 120.99(17) . . ?
O2 C11 N3 118.85(17) . . ?
N4 C11 N3 120.16(17) . . ?
N1 C1 C2 123.49(17) . . ?
N1 C1 C6 118.12(16) . . ?
C2 C1 C6 118.36(17) . . ?
C1 C2 H2 118.4(13) . . ?
C3 C2 C1 121.00(17) . . ?
C3 C2 H2 120.6(13) . . ?
C3 C4 C8 120.58(17) . . ?
C5 C4 C3 118.36(18) . . ?
C5 C4 C8 121.05(17) . . ?
O1 C10 N3 122.71(17) . . ?
O1 C10 C9 123.31(18) . . ?
N3 C10 C9 113.98(16) . . ?
N2 C6 C1 122.23(17) . . ?
N2 C6 C5 118.15(16) . . ?
C5 C6 C1 119.62(17) . . ?
O3 C14 C15 107.16(15) . . ?
O3 C14 C13 111.06(16) . . ?
O3 C14 H14 109.8(14) . . ?
C15 C14 H14 109.1(13) . . ?
C13 C14 C15 111.00(14) . . ?
C13 C14 H14 108.8(14) . . ?
C2 C3 C4 120.79(17) . . ?
C2 C3 C7 118.96(17) . . ?
C4 C3 C7 120.24(18) . . ?
C4 C5 C6 121.81(17) . . ?
C4 C5 H5A 122.8(13) . . ?
C6 C5 H5A 115.4(13) . . ?
O6 C17 C16 110.15(15) . . ?
O6 C17 H17A 108.7(15) . . ?
O6 C17 H17B 104.7(12) . . ?
C16 C17 H17A 109.7(14) . . ?
C16 C17 H17B 113.2(12) . . ?
H17A C17 H17B 110.3(18) . . ?
O5 C16 C15 108.50(14) . . ?
O5 C16 C17 107.84(14) . . ?
O5 C16 H16 110.9(12) . . ?
C15 C16 H16 108.1(13) . . ?
C17 C16 C15 113.15(15) . . ?
C17 C16 H16 108.4(12) . . ?
C4 C8 H8A 112.2(16) . . ?
C4 C8 H8B 113.1(15) . . ?
C4 C8 H8C 113.1(17) . . ?
H8A C8 H8B 110(2) . . ?
H8A C8 H8C 102(2) . . ?
H8B C8 H8C 105(2) . . ?
C3 C7 H7A 110.7(14) . . ?
C3 C7 H7B 111.0(15) . . ?
C3 C7 H7C 108.5(15) . . ?
H7A C7 H7B 111(2) . . ?
H7A C7 H7C 106(2) . . ?
H7B C7 H7C 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C15 C14 O3 -67.61(18) . . . . ?
O4 C15 C14 C13 53.8(2) . . . . ?
O4 C15 C16 O5 -178.56(14) . . . . ?
O4 C15 C16 C17 61.81(18) . . . . ?
O6 C17 C16 O5 65.28(18) . . . . ?
O6 C17 C16 C15 -174.71(14) . . . . ?
N1 C12 C9 N2 2.8(3) . . . . ?
N1 C12 C9 C10 -176.05(16) . . . . ?
N1 C13 C14 O3 -51.5(2) . . . . ?
N1 C13 C14 C15 -170.61(15) . . . . ?
N1 C1 C2 C3 177.66(17) . . . . ?
N1 C1 C6 N2 0.5(3) . . . . ?
N1 C1 C6 C5 -179.54(16) . . . . ?
N4 C12 C9 N2 -177.02(17) . . . . ?
N4 C12 C9 C10 4.2(3) . . . . ?
N2 C9 C10 O1 -5.2(3) . . . . ?
N2 C9 C10 N3 175.02(17) . . . . ?
N2 C6 C5 C4 -178.62(17) . . . . ?
C12 N1 C13 C14 -80.7(2) . . . . ?
C12 N1 C1 C2 -175.82(16) . . . . ?
C12 N1 C1 C6 2.1(2) . . . . ?
C12 N4 C11 O2 172.62(16) . . . . ?
C12 N4 C11 N3 -7.4(2) . . . . ?
C12 C9 C10 O1 173.67(19) . . . . ?
C12 C9 C10 N3 -6.1(2) . . . . ?
C9 N2 C6 C1 -1.4(3) . . . . ?
C9 N2 C6 C5 178.61(17) . . . . ?
C13 N1 C12 N4 -5.0(2) . . . . ?
C13 N1 C12 C9 175.21(16) . . . . ?
C13 N1 C1 C2 5.4(3) . . . . ?
C13 N1 C1 C6 -176.61(15) . . . . ?
C11 N4 C12 N1 -177.03(16) . . . . ?
C11 N4 C12 C9 2.7(3) . . . . ?
C11 N3 C10 O1 -177.96(19) . . . . ?
C11 N3 C10 C9 1.8(3) . . . . ?
C1 N1 C12 N4 176.18(16) . . . . ?
C1 N1 C12 C9 -3.6(2) . . . . ?
C1 N1 C13 C14 98.09(19) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C1 C2 C3 C7 -177.16(17) . . . . ?
C1 C6 C5 C4 1.4(3) . . . . ?
C2 C1 C6 N2 178.59(16) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C10 N3 C11 O2 -174.86(17) . . . . ?
C10 N3 C11 N4 5.2(3) . . . . ?
C6 N2 C9 C12 -0.2(3) . . . . ?
C6 N2 C9 C10 178.57(16) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C14 C15 C16 O5 -55.52(18) . . . . ?
C14 C15 C16 C17 -175.15(14) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C5 C4 C3 C2 -2.2(3) . . . . ?
C5 C4 C3 C7 177.12(17) . . . . ?
C16 C15 C14 O3 169.05(15) . . . . ?
C16 C15 C14 C13 -69.53(19) . . . . ?
C8 C4 C3 C2 179.21(17) . . . . ?
C8 C4 C3 C7 -1.5(3) . . . . ?
C8 C4 C5 C6 178.99(17) . . . . ?

_olex2_date_sample_data_collection 2022-06-07
_olex2_date_sample_submission    2022-06-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder inert oil'
_olex2_submission_original_sample_id 'Cinnamic acid/ Riboflavin/ ACN'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.685
_oxdiff_exptl_absorpt_empirical_full_min 0.446
