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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_R_C
_database_code_depnum_ccdc_archive 'CCDC 2168404'
loop_
_audit_author_name
_audit_author_address
'Vera Vasylyeva'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-04-24 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;

_audit_creation_date             2021-11-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'roseolumiflavin 2,4-diaminopyrimidine'
_chemical_name_systematic        
'8-(dimethylamino)-7,10-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione 2,4-diaminopyrimidine'
_chemical_formula_moiety         'C14 H15 N5 O2, C4 H6 N4'
_chemical_formula_sum            'C18 H21 N9 O2'
_chemical_formula_weight         395.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H21N9O2
_chemical_oxdiff_usercomment     'solvent methanol'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0245(5)
_cell_length_b                   8.4915(5)
_cell_length_c                   14.9566(7)
_cell_angle_alpha                87.548(5)
_cell_angle_beta                 74.813(5)
_cell_angle_gamma                65.130(6)
_cell_volume                     889.69(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2623
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      77.1500
_cell_measurement_theta_min      3.0740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (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 orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0093
0 1 0 0.0206
1 2 0 0.0280
-2 -1 -1 0.0392
2 1 1 0.0205
0 1 -1 0.0262
0 -2 1 0.0056
0 0 -1 0.0242
0 0 1 0.0056
-1 4 4 0.0187
2 5 5 0.0176
0 1 2 0.0112

_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.03
_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
0.0015 -0.9979 -0.0051 0.0564 0.1915 -0.0169
-0.0015 0.9979 0.0051 -0.0564 -0.1915 0.0169
0.9964 1.9981 0.0048 -0.1384 -0.2619 0.2151
-1.9977 -1.0018 -0.9942 0.0075 -0.0128 -0.3839
1.9977 1.0018 0.9942 -0.0075 0.0128 0.3839
-0.0018 0.9985 -0.9948 -0.1564 -0.1536 0.0125
0.0034 -1.9965 0.9897 0.2129 0.3450 -0.0294
-0.0003 0.0006 -0.9999 -0.1000 0.0379 -0.0043
0.0003 -0.0006 0.9999 0.1000 -0.0379 0.0043
-1.0362 3.7138 3.6866 0.1821 -0.9772 -0.1087
2.3030 4.8550 4.9329 0.1586 -0.8380 0.5222
-0.0009 0.9967 2.0049 0.1435 -0.2673 0.0255

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12348
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.995
_diffrn_reflns_theta_min         3.071
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -57.00   0.50   30.00    --  -51.27 141.00   8.00   82
  2  ω   -123.00 -71.00   0.50   30.00    --  -51.27-129.00 123.00  104
  3  ω    -79.00 -51.00   0.50   30.00    --  -51.27 129.00-163.00   56
  4  ω   -109.00 -64.00   0.50   30.00    --  -51.27-141.00 -49.00   90
  5  ω     62.00  98.00   0.50   30.00    --   51.27-141.00 -49.00   72
  6  ω     39.00  64.00   0.50   30.00    --   51.27-129.00 123.00   50
  7  ω   -110.00 -65.00   0.50  100.00    --  -90.00-141.00 -49.00   90
  8  ω    -69.00 -37.00   0.50  100.00    --  -90.00 129.00-163.00   64
  9  ω    -84.00 -58.00   0.50  100.00    --  -90.00 141.00   8.00   52
 10  ω     84.00 150.00   0.50  100.00    --  109.91 141.00   8.00  132
 11  ω     82.00 112.00   0.50  100.00    --  109.91-129.00 123.00   60
 12  ω     62.00  89.00   0.50  100.00    --  109.91-141.00 -49.00   54
 13  ω     97.00 148.00   0.50  100.00    --  109.91 129.00-163.00  102
 14  ω     92.00 124.00   0.50  100.00    --  109.91-141.00 -49.00   64
 15  ω    -31.00  11.00   0.50   30.00    --  -51.27  19.00 150.00   84
 16  ω    -18.00   7.00   0.50   30.00    --  -51.27  19.00 -90.00   50
 17  ω    -22.00   5.00   0.50   30.00    --  -51.27  19.00 -60.00   54
 18  ω   -104.00 -76.00   0.50   30.00    --  -51.27-125.00 -30.00   56
 19  ω    -48.00  19.00   0.50   30.00    --  -51.27  38.00-150.00  134
 20  ω    -23.00   2.00   0.50   30.00    --  -51.27  19.00-180.00   50
 21  ω    -48.00 -21.00   0.50  100.00    --  -90.00  38.00 -30.00   54
 22  ω    -48.00 -20.00   0.50  100.00    --  -90.00  38.00-180.00   56
 23  ω   -160.00-106.00   0.50  100.00    --  -90.00 -38.00 120.00  108
 24  ω    -48.00 -23.00   0.50  100.00    --  -90.00  38.00 -90.00   50
 25  ω    -69.00 -19.00   0.50  100.00    --  -90.00  57.00  60.00  100
 26  ω    -46.00 -19.00   0.50  100.00    --  -90.00  38.00  60.00   54
 27  ω   -136.00-106.00   0.50  100.00    --  -90.00   0.00 -30.00   60
 28  ω   -140.00-115.00   0.50  100.00    --  -90.00-129.00 123.00   50
 29  ω    -64.00 -18.00   0.50  100.00    --  -90.00  57.00   0.00   92
 30  ω   -119.00 -89.00   0.50  100.00    --  -90.00 -19.00-180.00   60
 31  ω   -162.00-135.00   0.50  100.00    --  -90.00 -19.00-180.00   54
 32  ω    -71.00 -32.00   0.50  100.00    --  -90.00  57.00 120.00   78
 33  ω    -48.00 -22.00   0.50  100.00    --  -90.00  38.00-120.00   52
 34  ω    -46.00 -19.00   0.50  100.00    --  -90.00  38.00-150.00   54
 35  ω     95.00 123.00   0.50  100.00    --  109.91 125.00 -30.00   56
 36  ω     45.00 103.00   0.50  100.00    --  109.91-125.00-150.00  116
 37  ω     57.00 111.00   0.50  100.00    --  109.91-125.00-120.00  108
 38  ω     72.00 106.00   0.50  100.00    --  109.91-125.00  30.00   68
 39  ω    117.00 174.00   0.50  100.00    --  109.91  38.00 -60.00  114
 40  ω     64.00  90.00   0.50  100.00    --  109.91 -77.00 -60.00   52
 41  ω     38.00  96.00   0.50  100.00    --  109.91 -77.00 -90.00  116
 42  ω     79.00 105.00   0.50  100.00    --  109.91 -99.00 120.00   52
 43  ω     38.00  75.00   0.50  100.00    --  109.91 -99.00 120.00   74
 44  ω    142.00 168.00   0.50  100.00    --  109.91 125.00 -30.00   52
 45  ω     78.00 104.00   0.50  100.00    --  109.91 -99.00  30.00   52
 46  ω     47.00  74.00   0.50  100.00    --  109.91 -77.00 -30.00   54
 47  ω     42.00  79.00   0.50  100.00    --  109.91 -77.00 120.00   74
 48  ω     70.00  97.00   0.50  100.00    --  109.91 -77.00-120.00   54
 49  ω     79.00 106.00   0.50  100.00    --  109.91-125.00  60.00   54
 50  ω     45.00  70.00   0.50  100.00    --  109.91 -99.00  30.00   50
 51  ω     42.00  67.00   0.50  100.00    --  109.91 -77.00-120.00   50
 52  ω     81.00  82.00   0.50  100.00    --  109.91 -99.00  90.00    2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0248521000
_diffrn_orient_matrix_UB_12      -0.0571162000
_diffrn_orient_matrix_UB_13      0.0999605000
_diffrn_orient_matrix_UB_21      0.1213569000
_diffrn_orient_matrix_UB_22      -0.1914926000
_diffrn_orient_matrix_UB_23      -0.0380638000
_diffrn_orient_matrix_UB_31      0.1814635000
_diffrn_orient_matrix_UB_32      0.0171435000
_diffrn_orient_matrix_UB_33      0.0042596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2285
_reflns_number_total             3599
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.006
_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)+(0.0958P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1678
_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
O1 O 0.7681(3) 0.7729(2) 0.57781(13) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.8942(3) 0.2835(2) 0.73306(13) 0.0308(4) Uani 1 1 d . . . . .
N2 N 0.8292(3) 0.5269(3) 0.65449(15) 0.0240(4) Uani 1 1 d . . . . .
N4 N 0.7439(3) 0.2737(2) 0.45890(14) 0.0246(4) Uani 1 1 d . . . . .
N6 N 0.8759(3) 0.7088(2) 0.80227(14) 0.0248(4) Uani 1 1 d . . . . .
N8 N 0.9255(3) 0.4658(3) 0.88610(16) 0.0273(5) Uani 1 1 d . . . . .
N3 N 0.8210(3) 0.2720(3) 0.59810(14) 0.0260(5) Uani 1 1 d . . . . .
N1 N 0.7195(3) 0.6110(2) 0.43492(15) 0.0248(4) Uani 1 1 d . . . . .
N7 N 0.9352(3) 0.7002(3) 0.95249(15) 0.0274(5) Uani 1 1 d . . . . .
N5 N 0.6025(3) 0.2652(3) 0.16750(15) 0.0283(5) Uani 1 1 d . . . . .
N9 N 0.8307(3) 0.9510(3) 0.71897(16) 0.0279(5) Uani 1 1 d . . . . .
C10 C 0.6960(3) 0.5245(3) 0.36973(17) 0.0243(5) Uani 1 1 d . . . . .
C1 C 0.7592(3) 0.5296(3) 0.50917(17) 0.0242(5) Uani 1 1 d . . . . .
C4 C 0.7777(3) 0.3552(3) 0.52487(18) 0.0244(5) Uani 1 1 d . . . . .
C18 C 0.8646(3) 0.8717(3) 0.79600(17) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.7054(3) 0.3532(3) 0.37962(17) 0.0234(5) Uani 1 1 d . . . . .
C7 C 0.6328(3) 0.3545(3) 0.23057(18) 0.0253(5) Uani 1 1 d . . . . .
C6 C 0.6754(3) 0.2720(3) 0.31082(18) 0.0253(5) Uani 1 1 d . . . . .
C8 C 0.6170(3) 0.5317(3) 0.22111(18) 0.0259(5) Uani 1 1 d . . . . .
C17 C 0.8852(3) 0.9565(3) 0.86857(18) 0.0265(5) Uani 1 1 d . . . . .
C15 C 0.9128(3) 0.6302(3) 0.87946(18) 0.0254(5) Uani 1 1 d . . . . .
C3 C 0.8504(3) 0.3549(3) 0.66358(17) 0.0253(5) Uani 1 1 d . . . . .
C9 C 0.6506(3) 0.6062(3) 0.28997(18) 0.0264(5) Uani 1 1 d . . . . .
C16 C 0.9174(4) 0.8647(3) 0.94422(19) 0.0285(5) Uani 1 1 d . . . . .
C2 C 0.7846(3) 0.6213(3) 0.58108(17) 0.0246(5) Uani 1 1 d . . . . .
C11 C 0.7439(4) 0.1004(3) 0.4740(2) 0.0295(6) Uani 1 1 d . . . . .
C13 C 0.5966(4) 0.0983(4) 0.1896(2) 0.0333(6) Uani 1 1 d . . . . .
C12 C 0.5573(4) 0.6436(3) 0.1435(2) 0.0321(6) Uani 1 1 d . . . . .
C14 C 0.5972(4) 0.3104(4) 0.0725(2) 0.0340(6) Uani 1 1 d . . . . .
H17 H 0.871(4) 1.081(4) 0.863(2) 0.027(7) Uiso 1 1 d . . . . .
H6 H 0.691(4) 0.149(4) 0.317(2) 0.030(7) Uiso 1 1 d . . . . .
H16 H 0.940(4) 0.906(4) 1.003(2) 0.025(7) Uiso 1 1 d . . . . .
H13A H 0.549(4) 0.072(5) 0.143(2) 0.044(9) Uiso 1 1 d . . . . .
H9 H 0.642(4) 0.726(4) 0.286(2) 0.029(7) Uiso 1 1 d . . . . .
H11A H 0.620(4) 0.108(4) 0.4702(19) 0.024(6) Uiso 1 1 d . . . . .
H11B H 0.756(5) 0.071(6) 0.536(3) 0.069(11) Uiso 1 1 d . . . . .
H9A H 0.815(4) 0.897(4) 0.667(2) 0.038(8) Uiso 1 1 d . . . . .
H14A H 0.688(4) 0.361(4) 0.047(2) 0.035(7) Uiso 1 1 d . . . . .
H8A H 0.928(4) 0.407(5) 0.830(2) 0.045(9) Uiso 1 1 d . . . . .
H13B H 0.716(4) 0.013(4) 0.187(2) 0.030(7) Uiso 1 1 d . . . . .
H12A H 0.447(4) 0.638(4) 0.129(2) 0.035(8) Uiso 1 1 d . . . . .
H14B H 0.470(5) 0.381(5) 0.068(2) 0.045(9) Uiso 1 1 d . . . . .
H9B H 0.849(5) 1.047(5) 0.708(2) 0.050(9) Uiso 1 1 d . . . . .
H13C H 0.507(4) 0.106(4) 0.251(2) 0.040(8) Uiso 1 1 d . . . . .
H2 H 0.848(5) 0.578(5) 0.703(3) 0.049(9) Uiso 1 1 d . . . . .
H12B H 0.658(5) 0.609(5) 0.083(3) 0.051(9) Uiso 1 1 d . . . . .
H8B H 0.966(4) 0.414(4) 0.933(2) 0.031(8) Uiso 1 1 d . . . . .
H11C H 0.847(5) 0.015(5) 0.427(3) 0.051(9) Uiso 1 1 d . . . . .
H12C H 0.525(4) 0.769(5) 0.164(2) 0.045(8) Uiso 1 1 d . . . . .
H14C H 0.640(5) 0.193(5) 0.033(3) 0.056(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.238(3) . ?
O2 C3 1.237(3) . ?
N2 C3 1.402(3) . ?
N2 C2 1.366(3) . ?
N2 H2 0.93(4) . ?
N4 C4 1.373(3) . ?
N4 C5 1.380(3) . ?
N4 C11 1.479(3) . ?
N6 C18 1.348(3) . ?
N6 C15 1.347(3) . ?
N8 C15 1.358(3) . ?
N8 H8A 0.99(4) . ?
N8 H8B 0.87(3) . ?
N3 C4 1.322(3) . ?
N3 C3 1.353(3) . ?
N1 C10 1.341(3) . ?
N1 C1 1.322(3) . ?
N7 C15 1.352(3) . ?
N7 C16 1.346(3) . ?
N5 C7 1.364(3) . ?
N5 C13 1.458(3) . ?
N5 C14 1.463(3) . ?
N9 C18 1.341(3) . ?
N9 H9A 0.97(3) . ?
N9 H9B 0.89(4) . ?
C10 C5 1.428(3) . ?
C10 C9 1.407(3) . ?
C1 C4 1.440(3) . ?
C1 C2 1.457(3) . ?
C18 C17 1.409(3) . ?
C5 C6 1.387(3) . ?
C7 C6 1.411(3) . ?
C7 C8 1.460(3) . ?
C6 H6 1.00(3) . ?
C8 C9 1.370(4) . ?
C8 C12 1.514(3) . ?
C17 C16 1.365(4) . ?
C17 H17 1.01(3) . ?
C9 H9 0.99(3) . ?
C16 H16 1.04(3) . ?
C11 H11A 0.98(3) . ?
C11 H11B 0.97(4) . ?
C11 H11C 0.97(4) . ?
C13 H13A 0.96(3) . ?
C13 H13B 0.92(3) . ?
C13 H13C 0.99(3) . ?
C12 H12A 0.99(3) . ?
C12 H12B 1.00(4) . ?
C12 H12C 1.03(3) . ?
C14 H14A 0.98(3) . ?
C14 H14B 0.97(3) . ?
C14 H14C 1.06(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
C3 N2 H2 116(2) . . ?
C2 N2 C3 124.8(2) . . ?
C2 N2 H2 119(2) . . ?
C4 N4 C5 120.79(19) . . ?
C4 N4 C11 119.6(2) . . ?
C5 N4 C11 119.6(2) . . ?
C15 N6 C18 117.0(2) . . ?
C15 N8 H8A 117(2) . . ?
C15 N8 H8B 114(2) . . ?
H8A N8 H8B 126(3) . . ?
C4 N3 C3 118.3(2) . . ?
C1 N1 C10 117.6(2) . . ?
C16 N7 C15 114.5(2) . . ?
C7 N5 C13 119.2(2) . . ?
C7 N5 C14 125.7(2) . . ?
C13 N5 C14 114.6(2) . . ?
C18 N9 H9A 123.8(19) . . ?
C18 N9 H9B 118(2) . . ?
H9A N9 H9B 117(3) . . ?
N1 C10 C5 122.6(2) . . ?
N1 C10 C9 119.9(2) . . ?
C9 C10 C5 117.5(2) . . ?
N1 C1 C4 124.4(2) . . ?
N1 C1 C2 118.6(2) . . ?
C4 C1 C2 117.0(2) . . ?
N4 C4 C1 116.4(2) . . ?
N3 C4 N4 118.9(2) . . ?
N3 C4 C1 124.7(2) . . ?
N6 C18 C17 121.0(2) . . ?
N9 C18 N6 117.8(2) . . ?
N9 C18 C17 121.2(2) . . ?
N4 C5 C10 118.1(2) . . ?
N4 C5 C6 122.0(2) . . ?
C6 C5 C10 120.0(2) . . ?
N5 C7 C6 117.6(2) . . ?
N5 C7 C8 123.8(2) . . ?
C6 C7 C8 118.6(2) . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 118.7(16) . . ?
C7 C6 H6 119.3(17) . . ?
C7 C8 C12 125.3(2) . . ?
C9 C8 C7 117.6(2) . . ?
C9 C8 C12 117.1(2) . . ?
C18 C17 H17 119.7(16) . . ?
C16 C17 C18 116.4(2) . . ?
C16 C17 H17 123.9(16) . . ?
N6 C15 N8 117.4(2) . . ?
N6 C15 N7 126.3(2) . . ?
N7 C15 N8 116.3(2) . . ?
O2 C3 N2 118.2(2) . . ?
O2 C3 N3 121.6(2) . . ?
N3 C3 N2 120.2(2) . . ?
C10 C9 H9 115.4(17) . . ?
C8 C9 C10 124.4(2) . . ?
C8 C9 H9 120.2(17) . . ?
N7 C16 C17 124.7(2) . . ?
N7 C16 H16 108.7(15) . . ?
C17 C16 H16 126.4(15) . . ?
O1 C2 N2 121.2(2) . . ?
O1 C2 C1 123.9(2) . . ?
N2 C2 C1 114.9(2) . . ?
N4 C11 H11A 108.0(16) . . ?
N4 C11 H11B 109(2) . . ?
N4 C11 H11C 110(2) . . ?
H11A C11 H11B 108(3) . . ?
H11A C11 H11C 111(3) . . ?
H11B C11 H11C 111(3) . . ?
N5 C13 H13A 105(2) . . ?
N5 C13 H13B 111.6(17) . . ?
N5 C13 H13C 112.1(18) . . ?
H13A C13 H13B 110(3) . . ?
H13A C13 H13C 108(3) . . ?
H13B C13 H13C 110(3) . . ?
C8 C12 H12A 113.0(18) . . ?
C8 C12 H12B 114(2) . . ?
C8 C12 H12C 107.2(19) . . ?
H12A C12 H12B 104(3) . . ?
H12A C12 H12C 110(2) . . ?
H12B C12 H12C 109(3) . . ?
N5 C14 H14A 110.1(17) . . ?
N5 C14 H14B 113(2) . . ?
N5 C14 H14C 107(2) . . ?
H14A C14 H14B 114(3) . . ?
H14A C14 H14C 109(3) . . ?
H14B C14 H14C 104(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C17 H17 O2 1.01(3) 2.57(3) 3.381(3) 137(2) 1_565 yes
C11 H11B O1 0.97(4) 2.54(4) 3.084(3) 115(3) 1_545 yes
N9 H9A O1 0.97(3) 1.95(3) 2.909(3) 172(3) . yes
N8 H8A O2 0.99(4) 1.96(4) 2.938(3) 170(3) . yes
N9 H9B O2 0.89(4) 2.24(4) 3.097(3) 160(3) 1_565 yes
N9 H9B N3 0.89(4) 2.44(4) 3.190(3) 141(3) 1_565 yes
N2 H2 N6 0.93(4) 2.01(4) 2.937(3) 175(3) . yes
N8 H8B N7 0.87(3) 2.11(3) 2.977(3) 177(3) 2_767 yes
C11 H11C N3 0.97(4) 2.70(4) 3.519(4) 143(3) 2_756 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C5 C6 C7 178.9(2) . . . . ?
N6 C18 C17 C16 0.2(3) . . . . ?
N1 C10 C5 N4 -1.3(3) . . . . ?
N1 C10 C5 C6 178.5(2) . . . . ?
N1 C10 C9 C8 -177.5(2) . . . . ?
N1 C1 C4 N4 -2.6(3) . . . . ?
N1 C1 C4 N3 178.6(2) . . . . ?
N1 C1 C2 O1 1.2(4) . . . . ?
N1 C1 C2 N2 -178.7(2) . . . . ?
N5 C7 C6 C5 -178.9(2) . . . . ?
N5 C7 C8 C9 179.7(2) . . . . ?
N5 C7 C8 C12 2.8(4) . . . . ?
N9 C18 C17 C16 179.3(2) . . . . ?
C10 N1 C1 C4 -0.4(3) . . . . ?
C10 N1 C1 C2 -179.8(2) . . . . ?
C10 C5 C6 C7 -0.9(3) . . . . ?
C1 N1 C10 C5 2.4(3) . . . . ?
C1 N1 C10 C9 179.0(2) . . . . ?
C4 N4 C5 C10 -1.9(3) . . . . ?
C4 N4 C5 C6 178.3(2) . . . . ?
C4 N3 C3 O2 -178.9(2) . . . . ?
C4 N3 C3 N2 1.9(3) . . . . ?
C4 C1 C2 O1 -178.2(2) . . . . ?
C4 C1 C2 N2 1.9(3) . . . . ?
C18 N6 C15 N8 -179.6(2) . . . . ?
C18 N6 C15 N7 1.7(4) . . . . ?
C18 C17 C16 N7 1.8(4) . . . . ?
C5 N4 C4 N3 -177.5(2) . . . . ?
C5 N4 C4 C1 3.6(3) . . . . ?
C5 C10 C9 C8 -0.7(4) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
C6 C7 C8 C12 -175.0(2) . . . . ?
C8 C7 C6 C5 -1.0(3) . . . . ?
C15 N6 C18 N9 179.0(2) . . . . ?
C15 N6 C18 C17 -1.8(3) . . . . ?
C15 N7 C16 C17 -1.9(4) . . . . ?
C3 N2 C2 O1 180.0(2) . . . . ?
C3 N2 C2 C1 -0.1(3) . . . . ?
C3 N3 C4 N4 -178.7(2) . . . . ?
C3 N3 C4 C1 0.0(4) . . . . ?
C9 C10 C5 N4 -178.0(2) . . . . ?
C9 C10 C5 C6 1.7(3) . . . . ?
C16 N7 C15 N6 0.1(3) . . . . ?
C16 N7 C15 N8 -178.6(2) . . . . ?
C2 N2 C3 O2 178.9(2) . . . . ?
C2 N2 C3 N3 -2.0(4) . . . . ?
C2 C1 C4 N4 176.8(2) . . . . ?
C2 C1 C4 N3 -2.0(3) . . . . ?
C11 N4 C4 N3 4.0(3) . . . . ?
C11 N4 C4 C1 -174.8(2) . . . . ?
C11 N4 C5 C10 176.5(2) . . . . ?
C11 N4 C5 C6 -3.2(3) . . . . ?
C13 N5 C7 C6 6.0(3) . . . . ?
C13 N5 C7 C8 -171.7(2) . . . . ?
C12 C8 C9 C10 176.1(2) . . . . ?
C14 N5 C7 C6 -166.1(2) . . . . ?
C14 N5 C7 C8 16.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.845
_oxdiff_exptl_absorpt_empirical_full_min 0.617
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_R
_database_code_depnum_ccdc_archive 'CCDC 2168405'
loop_
_audit_author_name
_audit_author_address
'Vera Vasylyeva'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-04-24 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
8-(dimethylamino)-7,10-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione
_chemical_name_common            roseolumiflavin
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N5 O2'
_chemical_formula_sum            'C14 H15 N5 O2'
_chemical_formula_weight         285.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7469(10)
_cell_length_b                   7.0326(8)
_cell_length_c                   14.3336(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.135(5)
_cell_angle_gamma                90
_cell_volume                     1268.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2214
_cell_measurement_theta_min      3.235
_cell_measurement_theta_max      27.427

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8604
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2224
_reflns_number_gt                1595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0842P)²+0.2024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2224
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63050(11) 0.2878(3) 0.61660(11) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.9399(19) 0.440(3) 0.5624(15) 0.033(6) Uiso 1 1 d . . . . .
O1 O 0.84301(9) 0.3677(2) 0.68951(9) 0.0330(4) Uani 1 1 d . . . . .
C1 C 0.70103(13) 0.3270(3) 0.56088(13) 0.0211(5) Uani 1 1 d . . . . .
O2 O 0.91741(9) 0.4527(3) 0.39444(9) 0.0425(5) Uani 1 1 d . . . . .
H2 H 0.3744(14) 0.215(3) 0.3731(15) 0.026(5) Uiso 1 1 d . . . . .
C2 C 0.81091(14) 0.3678(3) 0.60457(13) 0.0228(5) Uani 1 1 d . . . . .
N2 N 0.87696(12) 0.4084(3) 0.54072(11) 0.0277(5) Uani 1 1 d . . . . .
C3 C 0.84825(14) 0.4126(3) 0.44280(14) 0.0284(6) Uani 1 1 d . . . . .
N3 N 0.74730(11) 0.3730(3) 0.40302(11) 0.0258(5) Uani 1 1 d . . . . .
H3 H 0.4761(14) 0.204(3) 0.7006(14) 0.024(5) Uiso 1 1 d . . . . .
N4 N 0.57478(11) 0.2980(3) 0.42008(10) 0.0220(4) Uani 1 1 d . . . . .
H4C H 0.4831(18) 0.385(3) 0.2994(15) 0.037(6) Uiso 1 1 d . . . . .
H4B H 0.522(2) 0.176(4) 0.2888(18) 0.056(8) Uiso 1 1 d . . . . .
H4A H 0.6052(18) 0.347(3) 0.2902(15) 0.038(6) Uiso 1 1 d . . . . .
C4 C 0.67766(13) 0.3342(3) 0.46019(13) 0.0211(5) Uani 1 1 d . . . . .
C14 C 0.12318(17) 0.1102(6) 0.49436(18) 0.0532(10) Uani 1 1 d . . . . .
C13 C 0.19329(16) 0.1307(5) 0.34686(15) 0.0379(7) Uani 1 1 d . . . . .
C12 C 0.27760(16) 0.1273(4) 0.66854(15) 0.0326(6) Uani 1 1 d . . . . .
C11 C 0.54449(15) 0.3056(4) 0.31628(13) 0.0281(6) Uani 1 1 d . . . . .
C10 C 0.53064(13) 0.2518(3) 0.57506(12) 0.0211(5) Uani 1 1 d . . . . .
H6C H 0.128(2) 0.096(4) 0.330(2) 0.072(9) Uiso 1 1 d . . . . .
H6B H 0.243(2) 0.037(4) 0.3221(19) 0.063(8) Uiso 1 1 d . . . . .
H6A H 0.202(2) 0.269(4) 0.3202(19) 0.062(8) Uiso 1 1 d . . . . .
C6 C 0.39447(13) 0.2146(3) 0.43738(13) 0.0230(5) Uani 1 1 d . . . . .
N5 N 0.21646(11) 0.1372(3) 0.45046(11) 0.0253(5) Uani 1 1 d . . . . .
H5C H 0.2413(19) 0.005(4) 0.6582(17) 0.052(8) Uiso 1 1 d . . . . .
H5B H 0.2214(19) 0.223(4) 0.6725(16) 0.048(7) Uiso 1 1 d . . . . .
H5A H 0.3247(19) 0.123(4) 0.7306(18) 0.049(7) Uiso 1 1 d . . . . .
C5 C 0.49835(13) 0.2541(3) 0.47536(12) 0.0201(5) Uani 1 1 d . . . . .
C8 C 0.34872(13) 0.1699(3) 0.59688(13) 0.0235(5) Uani 1 1 d . . . . .
C7 C 0.31700(13) 0.1726(3) 0.49440(13) 0.0210(5) Uani 1 1 d . . . . .
H7C H 0.121(2) 0.183(5) 0.554(3) 0.088(10) Uiso 1 1 d . . . . .
H7B H 0.113(3) -0.010(6) 0.512(3) 0.112(16) Uiso 1 1 d . . . . .
H7A H 0.065(3) 0.156(5) 0.447(2) 0.079(9) Uiso 1 1 d . . . . .
C9 C 0.45246(14) 0.2069(3) 0.63169(13) 0.0244(5) Uani 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
N1 C1 1.323(2) . ?
N1 C10 1.341(2) . ?
O1 C2 1.221(2) . ?
C1 C4 1.428(3) . ?
C1 C2 1.469(2) . ?
O2 C3 1.237(2) . ?
C2 N2 1.369(2) . ?
N2 C3 1.393(2) . ?
N2 H1 0.84(2) . ?
C3 N3 1.351(2) . ?
N3 C4 1.328(2) . ?
N4 C4 1.370(2) . ?
N4 C5 1.385(2) . ?
N4 C11 1.478(2) . ?
C14 N5 1.443(3) . ?
C14 H7C 1.00(4) . ?
C14 H7B 0.90(4) . ?
C14 H7A 0.98(3) . ?
C13 N5 1.468(3) . ?
C13 H6C 0.87(3) . ?
C13 H6B 1.01(3) . ?
C13 H6A 1.06(3) . ?
C12 C8 1.504(3) . ?
C12 H5C 0.98(3) . ?
C12 H5B 0.99(2) . ?
C12 H5A 0.99(3) . ?
C11 H4C 0.96(2) . ?
C11 H4B 1.01(3) . ?
C11 H4A 0.96(2) . ?
C10 C9 1.417(2) . ?
C10 C5 1.423(3) . ?
C6 C5 1.378(2) . ?
C6 C7 1.409(2) . ?
C6 H2 0.92(2) . ?
N5 C7 1.358(2) . ?
C8 C9 1.362(3) . ?
C8 C7 1.460(3) . ?
C9 H3 0.99(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C10 117.35(16) . . ?
N1 C1 C4 124.40(16) . . ?
N1 C1 C2 118.48(16) . . ?
C4 C1 C2 117.12(16) . . ?
O1 C2 N2 121.49(16) . . ?
O1 C2 C1 124.81(17) . . ?
N2 C2 C1 113.70(16) . . ?
C2 N2 C3 125.94(16) . . ?
C2 N2 H1 117.4(14) . . ?
C3 N2 H1 116.6(14) . . ?
O2 C3 N3 121.74(17) . . ?
O2 C3 N2 118.20(15) . . ?
N3 C3 N2 120.07(16) . . ?
C4 N3 C3 117.83(16) . . ?
C4 N4 C5 121.01(15) . . ?
C4 N4 C11 119.71(15) . . ?
C5 N4 C11 119.29(14) . . ?
N3 C4 N4 117.93(16) . . ?
N3 C4 C1 125.33(16) . . ?
N4 C4 C1 116.74(16) . . ?
N5 C14 H7C 116.1(18) . . ?
N5 C14 H7B 114(2) . . ?
H7C C14 H7B 102(3) . . ?
N5 C14 H7A 104.1(17) . . ?
H7C C14 H7A 108(3) . . ?
H7B C14 H7A 112(3) . . ?
N5 C13 H6C 108.3(19) . . ?
N5 C13 H6B 109.8(15) . . ?
H6C C13 H6B 110(3) . . ?
N5 C13 H6A 108.7(15) . . ?
H6C C13 H6A 108(2) . . ?
H6B C13 H6A 111(2) . . ?
C8 C12 H5C 113.3(14) . . ?
C8 C12 H5B 115.1(14) . . ?
H5C C12 H5B 105.9(19) . . ?
C8 C12 H5A 105.9(14) . . ?
H5C C12 H5A 108(2) . . ?
H5B C12 H5A 108(2) . . ?
N4 C11 H4C 110.3(13) . . ?
N4 C11 H4B 111.7(15) . . ?
H4C C11 H4B 105.1(19) . . ?
N4 C11 H4A 107.8(13) . . ?
H4C C11 H4A 114(2) . . ?
H4B C11 H4A 108.2(19) . . ?
N1 C10 C9 119.47(16) . . ?
N1 C10 C5 123.13(16) . . ?
C9 C10 C5 117.40(16) . . ?
C5 C6 C7 122.08(17) . . ?
C5 C6 H2 119.6(12) . . ?
C7 C6 H2 118.3(12) . . ?
C7 N5 C14 127.15(16) . . ?
C7 N5 C13 119.89(15) . . ?
C14 N5 C13 112.92(15) . . ?
C6 C5 N4 122.57(16) . . ?
C6 C5 C10 120.07(16) . . ?
N4 C5 C10 117.36(15) . . ?
C9 C8 C7 117.61(16) . . ?
C9 C8 C12 116.31(17) . . ?
C7 C8 C12 126.07(16) . . ?
N5 C7 C6 117.76(16) . . ?
N5 C7 C8 123.65(16) . . ?
C6 C7 C8 118.58(15) . . ?
C8 C9 C10 124.25(17) . . ?
C8 C9 H3 119.2(11) . . ?
C10 C9 H3 116.6(11) . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_R_B
_database_code_depnum_ccdc_archive 'CCDC 2168407'
loop_
_audit_author_name
_audit_author_address
'Vera Vasylyeva'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-04-24 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;

_audit_creation_date             2022-04-19
_audit_creation_method           'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'

_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'roseolumiflavin 1,4-diiodotetrafluorobenzene'
_chemical_name_systematic        
'8-(dimethylamino)-7,10-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione 1,4-diiodotetrafluorobenzene'
_chemical_formula_moiety         'C14 H15 N5 O2, 1.5(C6 F4 I2)'
_chemical_formula_sum            'C23 H15 F6 I3 N5 O2'
_chemical_formula_weight         888.10
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.7683(3)
_cell_length_b                   12.2451(5)
_cell_length_c                   14.6375(5)
_cell_angle_alpha                108.280(4)
_cell_angle_beta                 91.090(3)
_cell_angle_gamma                96.577(4)
_cell_volume                     1311.17(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      3.0850
_cell_measurement_theta_max      76.1020
_cell_measurement_temperature    100(2)
_shelx_estimated_absorpt_T_max   0.597
_shelx_estimated_absorpt_T_min   0.327
_exptl_absorpt_coefficient_mu    28.774
_exptl_absorpt_correction_T_min  0.55013
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.90a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    2.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             834
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15384
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.301
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4901
_reflns_number_total             5298
_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_data_collection       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         1.761
_refine_diff_density_min         -1.355
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.00020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.112
_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)+(0.0487P)²+3.3321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
I1 I 0.56973(4) 0.54215(3) 0.21626(2) 0.02842(10) Uani 1 1 d . . . . .
F1 F 0.7604(4) 0.3704(3) 0.0481(2) 0.0411(8) Uani 1 1 d . . . . .
O1 O 0.7002(5) 0.7323(3) 0.3753(2) 0.0309(7) Uani 1 1 d . . . . .
N1 N 0.8854(5) 0.8550(4) 0.4929(3) 0.0251(8) Uani 1 1 d . . . . .
C1 C 0.4767(7) 0.4125(4) 0.0880(3) 0.0275(10) Uani 1 1 d . . . . .
H1 H 0.891(6) 0.911(4) 0.459(4) 0.013(11) Uiso 1 1 d . . . . .
I2 I 0.25063(4) 0.10258(3) -0.20551(2) 0.02728(10) Uani 1 1 d . . . . .
F2 F 0.6403(4) 0.2023(3) -0.1130(2) 0.0349(7) Uani 1 1 d . . . . .
O2 O 1.0616(5) 0.9846(3) 0.6107(2) 0.0296(7) Uani 1 1 d . . . . .
N2 N 0.7207(5) 0.5575(4) 0.4594(3) 0.0248(8) Uani 1 1 d . . . . .
C2 C 0.3018(6) 0.3861(5) 0.0625(3) 0.0289(10) Uani 1 1 d . . . . .
H2 H 0.918(8) 0.447(5) 0.699(5) 0.034(16) Uiso 1 1 d . . . . .
I3 I 0.77454(4) -0.09867(3) -0.18645(2) 0.03217(11) Uani 1 1 d . . . . .
F3 F 0.0670(4) 0.2756(3) -0.0405(2) 0.0446(8) Uani 1 1 d . . . . .
N3 N 0.9232(5) 0.6192(3) 0.6314(3) 0.0231(8) Uani 1 1 d . . . . .
C3 C 0.2394(7) 0.2969(5) -0.0191(4) 0.0309(11) Uani 1 1 d . . . . .
H3 H 0.605(8) 0.354(5) 0.408(4) 0.025(14) Uiso 1 1 d . . . . .
F4 F 0.1875(4) 0.4471(3) 0.1185(2) 0.0426(8) Uani 1 1 d . . . . .
N4 N 0.9874(5) 0.8085(3) 0.6289(3) 0.0250(8) Uani 1 1 d . . . . .
C4 C 0.3505(7) 0.2321(4) -0.0797(3) 0.0264(10) Uani 1 1 d . . . . .
H4A H 1.096(9) 0.723(6) 0.735(5) 0.035(16) Uiso 1 1 d . . . . .
H4B H 0.966(9) 0.646(6) 0.773(5) 0.040(17) Uiso 1 1 d . . . . .
H4C H 1.128(8) 0.594(6) 0.705(4) 0.033(15) Uiso 1 1 d . . . . .
F5 F 0.8384(4) 0.0919(3) 0.0219(2) 0.0389(7) Uani 1 1 d . . . . .
N5 N 0.7719(6) 0.2335(4) 0.6454(3) 0.0309(9) Uani 1 1 d . . . . .
C5 C 0.5263(6) 0.2601(4) -0.0558(3) 0.0253(9) Uani 1 1 d . . . . .
H5A H 0.844(11) 0.326(8) 0.789(6) 0.06(2) Uiso 1 1 d . . . . .
H5B H 1.003(11) 0.306(7) 0.717(5) 0.06(2) Uiso 1 1 d . . . . .
H5C H 0.900(8) 0.201(6) 0.750(5) 0.034(16) Uiso 1 1 d . . . . .
F6 F 0.3724(4) -0.1706(3) -0.1628(2) 0.0355(7) Uani 1 1 d . . . . .
C6 C 0.5884(6) 0.3486(4) 0.0280(3) 0.0276(10) Uani 1 1 d . . . . .
H6 H 0.537(9) 0.137(6) 0.608(5) 0.039(17) Uiso 1 1 d . . . . .
H6A H 0.701(9) 0.060(6) 0.585(5) 0.044(18) Uiso 1 1 d . . . . .
H6B H 0.647(10) 0.115(7) 0.693(6) 0.05(2) Uiso 1 1 d . . . . .
C7 C 0.6110(7) -0.0416(5) -0.0746(3) 0.0283(10) Uani 1 1 d . . . . .
H7A H 0.667(10) 0.098(7) 0.445(5) 0.05(2) Uiso 1 1 d . . . . .
H7B H 0.565(10) 0.153(6) 0.378(6) 0.05(2) Uiso 1 1 d . . . . .
H7C H 0.471(12) 0.143(7) 0.466(6) 0.07(2) Uiso 1 1 d . . . . .
C8 C 0.6714(6) 0.0452(5) 0.0098(4) 0.0285(10) Uani 1 1 d . . . . .
C9 C 0.4384(6) -0.0860(4) -0.0828(3) 0.0274(10) Uani 1 1 d . . . . .
C10 C 0.9821(6) 0.8856(4) 0.5799(3) 0.0239(9) Uani 1 1 d . . . . .
C11 C 0.9067(6) 0.7016(4) 0.5878(3) 0.0229(9) Uani 1 1 d . . . . .
C12 C 0.8395(6) 0.5074(4) 0.5927(3) 0.0235(9) Uani 1 1 d . . . . .
C13 C 0.8500(6) 0.4238(4) 0.6360(3) 0.0261(9) Uani 1 1 d . . . . .
C14 C 0.7605(6) 0.3099(4) 0.5968(4) 0.0279(10) Uani 1 1 d . . . . .
C15 C 0.6654(6) 0.2800(4) 0.5033(4) 0.0286(10) Uani 1 1 d . . . . .
C16 C 0.6568(7) 0.3658(4) 0.4635(3) 0.0273(10) Uani 1 1 d . . . . .
C17 C 0.7376(6) 0.4812(4) 0.5046(3) 0.0249(9) Uani 1 1 d . . . . .
C18 C 0.8024(6) 0.6653(4) 0.5002(3) 0.0245(9) Uani 1 1 d . . . . .
C19 C 0.7872(6) 0.7494(4) 0.4494(3) 0.0246(9) Uani 1 1 d . . . . .
C20 C 1.0416(7) 0.6482(5) 0.7182(4) 0.0300(10) Uani 1 1 d . . . . .
C21 C 0.8919(7) 0.2640(5) 0.7306(4) 0.0362(12) Uani 1 1 d . . . . .
C22 C 0.6505(8) 0.1283(5) 0.6312(5) 0.0392(12) Uani 1 1 d . . . . .
C23 C 0.5871(8) 0.1591(5) 0.4436(4) 0.0353(12) Uani 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
I1 C1 2.094(5) . ?
F1 C6 1.341(6) . ?
O1 C19 1.214(6) . ?
N1 H1 0.97(5) . ?
N1 C10 1.388(6) . ?
N1 C19 1.378(6) . ?
C1 C2 1.376(7) . ?
C1 C6 1.375(7) . ?
I2 C4 2.083(5) . ?
F2 C5 1.337(6) . ?
O2 C10 1.236(6) . ?
N2 C17 1.319(6) . ?
N2 C18 1.342(6) . ?
C2 C3 1.376(7) . ?
C2 F4 1.346(6) . ?
I3 C7 2.085(5) . ?
F3 C3 1.346(6) . ?
N3 C11 1.368(6) . ?
N3 C12 1.383(6) . ?
N3 C20 1.478(6) . ?
C3 C4 1.381(7) . ?
N4 C10 1.357(6) . ?
N4 C11 1.332(6) . ?
C4 C5 1.380(7) . ?
F5 C8 1.342(6) . ?
N5 C14 1.351(7) . ?
N5 C21 1.466(7) . ?
N5 C22 1.462(7) . ?
C5 C6 1.391(7) . ?
F6 C9 1.342(6) . ?
C7 C8 1.384(7) . ?
C7 C9 1.376(7) . ?
C8 C9 1.384(7) 2_655 ?
C9 C8 1.384(7) 2_655 ?
C11 C18 1.420(6) . ?
C12 C13 1.371(7) . ?
C12 C17 1.428(7) . ?
C13 H2 1.00(7) . ?
C13 C14 1.420(7) . ?
C14 C15 1.463(7) . ?
C15 C16 1.357(7) . ?
C15 C23 1.512(7) . ?
C16 H3 0.86(6) . ?
C16 C17 1.415(7) . ?
C18 C19 1.460(7) . ?
C20 H4A 0.92(7) . ?
C20 H4B 1.02(7) . ?
C20 H4C 0.98(7) . ?
C21 H5A 1.05(9) . ?
C21 H5B 1.01(8) . ?
C21 H5C 0.90(7) . ?
C22 H6 0.97(7) . ?
C22 H6A 1.02(7) . ?
C22 H6B 0.97(8) . ?
C23 H7A 1.02(8) . ?
C23 H7B 0.94(8) . ?
C23 H7C 0.99(9) . ?

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
C10 N1 H1 117(3) . . ?
C19 N1 H1 117(3) . . ?
C19 N1 C10 125.3(4) . . ?
C2 C1 I1 121.2(4) . . ?
C6 C1 I1 120.9(4) . . ?
C6 C1 C2 117.9(4) . . ?
C17 N2 C18 117.4(4) . . ?
C3 C2 C1 121.4(5) . . ?
F4 C2 C1 120.0(4) . . ?
F4 C2 C3 118.6(4) . . ?
C11 N3 C12 121.4(4) . . ?
C11 N3 C20 119.3(4) . . ?
C12 N3 C20 119.2(4) . . ?
C2 C3 C4 121.2(5) . . ?
F3 C3 C2 118.6(5) . . ?
F3 C3 C4 120.2(4) . . ?
C11 N4 C10 117.8(4) . . ?
C3 C4 I2 119.7(4) . . ?
C5 C4 I2 122.5(4) . . ?
C5 C4 C3 117.7(4) . . ?
C14 N5 C21 119.8(4) . . ?
C14 N5 C22 124.8(5) . . ?
C22 N5 C21 114.4(4) . . ?
F2 C5 C4 120.4(4) . . ?
F2 C5 C6 118.7(4) . . ?
C4 C5 C6 120.9(5) . . ?
F1 C6 C1 120.9(4) . . ?
F1 C6 C5 118.1(4) . . ?
C1 C6 C5 121.0(5) . . ?
C8 C7 I3 121.0(4) . . ?
C9 C7 I3 121.5(4) . . ?
C9 C7 C8 117.5(5) . . ?
F5 C8 C7 120.1(5) . . ?
F5 C8 C9 118.8(5) . 2_655 ?
C9 C8 C7 121.1(5) 2_655 . ?
F6 C9 C7 120.3(4) . . ?
F6 C9 C8 118.3(4) . 2_655 ?
C7 C9 C8 121.4(5) . 2_655 ?
O2 C10 N1 117.9(4) . . ?
O2 C10 N4 121.7(4) . . ?
N4 C10 N1 120.4(4) . . ?
N3 C11 C18 116.4(4) . . ?
N4 C11 N3 119.0(4) . . ?
N4 C11 C18 124.6(4) . . ?
N3 C12 C17 117.1(4) . . ?
C13 C12 N3 122.8(4) . . ?
C13 C12 C17 120.1(4) . . ?
C12 C13 H2 117(4) . . ?
C12 C13 C14 122.3(5) . . ?
C14 C13 H2 120(4) . . ?
N5 C14 C13 118.9(5) . . ?
N5 C14 C15 123.1(5) . . ?
C13 C14 C15 117.9(4) . . ?
C14 C15 C23 125.1(5) . . ?
C16 C15 C14 117.6(5) . . ?
C16 C15 C23 117.1(5) . . ?
C15 C16 H3 122(4) . . ?
C15 C16 C17 124.8(5) . . ?
C17 C16 H3 113(4) . . ?
N2 C17 C12 123.4(4) . . ?
N2 C17 C16 119.6(4) . . ?
C16 C17 C12 117.0(5) . . ?
N2 C18 C11 124.2(4) . . ?
N2 C18 C19 117.6(4) . . ?
C11 C18 C19 118.1(4) . . ?
O1 C19 N1 120.7(4) . . ?
O1 C19 C18 125.8(4) . . ?
N1 C19 C18 113.5(4) . . ?
N3 C20 H4A 112(4) . . ?
N3 C20 H4B 106(4) . . ?
N3 C20 H4C 108(4) . . ?
H4A C20 H4B 106(6) . . ?
H4A C20 H4C 110(6) . . ?
H4B C20 H4C 115(5) . . ?
N5 C21 H5A 110(4) . . ?
N5 C21 H5B 108(4) . . ?
N5 C21 H5C 110(4) . . ?
H5A C21 H5B 104(6) . . ?
H5A C21 H5C 107(6) . . ?
H5B C21 H5C 117(6) . . ?
N5 C22 H6 111(4) . . ?
N5 C22 H6A 109(4) . . ?
N5 C22 H6B 107(5) . . ?
H6 C22 H6A 112(6) . . ?
H6 C22 H6B 112(6) . . ?
H6A C22 H6B 107(6) . . ?
H7A C23 H7B 107(6) . . ?
H7A C23 H7C 113(6) . . ?
H7B C23 H7C 104(7) . . ?
C15 C23 H7A 112(4) . . ?
C15 C23 H7B 112(5) . . ?
C15 C23 H7C 109(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 -176.5(4) . . . . ?
I1 C1 C2 F4 2.6(7) . . . . ?
I1 C1 C6 F1 -2.5(7) . . . . ?
I1 C1 C6 C5 178.1(4) . . . . ?
C1 C2 C3 F3 -179.7(5) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
I2 C4 C5 F2 -1.2(7) . . . . ?
I2 C4 C5 C6 178.8(4) . . . . ?
F2 C5 C6 F1 -1.0(7) . . . . ?
F2 C5 C6 C1 178.4(4) . . . . ?
N2 C18 C19 O1 3.7(7) . . . . ?
N2 C18 C19 N1 -175.5(4) . . . . ?
C2 C1 C6 F1 179.4(5) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C2 C3 C4 I2 -177.4(4) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
I3 C7 C8 F5 -1.8(7) . . . . ?
I3 C7 C8 C9 177.8(4) . . . 2_655 ?
I3 C7 C9 F6 2.1(7) . . . . ?
I3 C7 C9 C8 -177.8(4) . . . 2_655 ?
F3 C3 C4 I2 0.8(7) . . . . ?
F3 C3 C4 C5 178.0(5) . . . . ?
N3 C11 C18 N2 0.3(7) . . . . ?
N3 C11 C18 C19 -177.6(4) . . . . ?
N3 C12 C13 C14 178.6(4) . . . . ?
N3 C12 C17 N2 0.1(7) . . . . ?
N3 C12 C17 C16 178.0(4) . . . . ?
C3 C4 C5 F2 -178.3(5) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
F4 C2 C3 F3 1.2(8) . . . . ?
F4 C2 C3 C4 179.4(5) . . . . ?
N4 C11 C18 N2 -179.6(4) . . . . ?
N4 C11 C18 C19 2.4(7) . . . . ?
C4 C5 C6 F1 178.9(5) . . . . ?
C4 C5 C6 C1 -1.6(8) . . . . ?
N5 C14 C15 C16 177.1(5) . . . . ?
N5 C14 C15 C23 -7.7(8) . . . . ?
C6 C1 C2 C3 1.5(8) . . . . ?
C6 C1 C2 F4 -179.3(5) . . . . ?
C8 C7 C9 F6 -179.8(4) . . . . ?
C8 C7 C9 C8 0.3(8) . . . 2_655 ?
C9 C7 C8 F5 -179.9(4) . . . . ?
C9 C7 C8 C9 -0.3(8) . . . 2_655 ?
C10 N1 C19 O1 176.5(4) . . . . ?
C10 N1 C19 C18 -4.3(7) . . . . ?
C10 N4 C11 N3 174.1(4) . . . . ?
C10 N4 C11 C18 -5.9(7) . . . . ?
C11 N3 C12 C13 -178.3(4) . . . . ?
C11 N3 C12 C17 1.0(6) . . . . ?
C11 N4 C10 N1 4.3(7) . . . . ?
C11 N4 C10 O2 -176.0(4) . . . . ?
C11 C18 C19 O1 -178.2(5) . . . . ?
C11 C18 C19 N1 2.6(6) . . . . ?
C12 N3 C11 N4 178.8(4) . . . . ?
C12 N3 C11 C18 -1.2(6) . . . . ?
C12 C13 C14 N5 -177.6(4) . . . . ?
C12 C13 C14 C15 4.7(7) . . . . ?
C13 C12 C17 N2 179.5(4) . . . . ?
C13 C12 C17 C16 -2.7(7) . . . . ?
C13 C14 C15 C16 -5.3(7) . . . . ?
C13 C14 C15 C23 169.9(5) . . . . ?
C14 C15 C16 C17 2.0(7) . . . . ?
C15 C16 C17 N2 179.9(5) . . . . ?
C15 C16 C17 C12 2.0(7) . . . . ?
C17 N2 C18 C11 0.7(7) . . . . ?
C17 N2 C18 C19 178.7(4) . . . . ?
C17 C12 C13 C14 -0.7(7) . . . . ?
C18 N2 C17 C12 -1.0(7) . . . . ?
C18 N2 C17 C16 -178.8(4) . . . . ?
C19 N1 C10 O2 -178.8(4) . . . . ?
C19 N1 C10 N4 1.0(7) . . . . ?
C20 N3 C11 N4 -5.2(6) . . . . ?
C20 N3 C11 C18 174.8(4) . . . . ?
C20 N3 C12 C13 5.6(7) . . . . ?
C20 N3 C12 C17 -175.0(4) . . . . ?
C21 N5 C14 C13 -7.4(7) . . . . ?
C21 N5 C14 C15 170.1(5) . . . . ?
C22 N5 C14 C13 160.6(5) . . . . ?
C22 N5 C14 C15 -21.8(8) . . . . ?
C23 C15 C16 C17 -173.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_R_A
_database_code_depnum_ccdc_archive 'CCDC 2168406'
loop_
_audit_author_name
_audit_author_address
'Vera Vasylyeva'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-04-24 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2022-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'roseolumiflavin acetylenedicarboxylic acid'
_chemical_name_systematic        
'8-(dimethylamino)-7,10-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione but-2-ynedioic acid'
_chemical_formula_moiety         'C14 H15 N5 O2, C4 H2 O4'
_chemical_formula_sum            'C18 H17 N5 O6'
_chemical_formula_weight         399.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H17N5O6
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   6.9603(4)
_cell_length_b                   18.1475(7)
_cell_length_c                   28.0356(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3541.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2174
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.2990
_cell_measurement_theta_min      3.1490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.976
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (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 red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 1 0.1148
-2 0 -1 0.0636
0 1 2 0.0119
0 -1 -2 0.0067
0 0 1 0.0146
0 0 -1 0.0067
0 1 -2 0.0042
0 -1 1 0.0077

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.016
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
2.0004 0.0064 0.9946 -0.0458 -0.2295 0.3798
-2.0004 -0.0064 -0.9946 0.0458 0.2295 -0.3798
-0.0010 1.0000 2.0007 0.0616 0.0951 0.0803
0.0010 -1.0000 -2.0007 -0.0616 -0.0951 -0.0803
-0.0002 0.0002 1.0006 -0.0107 0.0430 0.0325
0.0002 -0.0002 -1.0006 0.0107 -0.0430 -0.0325
-0.0002 0.9992 -2.0018 0.1044 -0.0769 -0.0497
0.0004 -0.9994 1.0012 -0.0937 0.0339 0.0172

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14153
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.986
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -27.00   0.50  250.00    --  -90.00  51.00 155.00   70
  2  ω   -156.00 -99.00   0.50  250.00    --  -90.00 -51.00   9.00  114
  3  ω   -138.00 -87.00   0.50  250.00    --  -90.00-113.00 140.00  102
  4  ω    -65.00 -24.00   0.50  250.00    --  -90.00  72.00 -10.00   82
  5  ω     37.00  86.00   0.50  250.00    --  109.41 -72.00-140.00   98
  6  ω    -25.00   1.00   0.50  100.00    --  -49.27  19.00 120.00   52
  7  ω    -29.00  25.00   0.50  100.00    --  -49.27  19.00-120.00  108
  8  ω     -5.00  24.00   0.50  100.00    --   49.27 -38.00 150.00   58
  9  ω    -23.00  21.00   0.50  100.00    --   49.27 -19.00-120.00   88
 10  ω    -13.00  17.00   0.50  100.00    --   49.27 -19.00-150.00   60
 11  ω    -44.00 -18.00   0.50  250.00    --  -90.00  38.00-180.00   52
 12  ω    -47.00 -21.00   0.50  250.00    --  -90.00  38.00 120.00   52
 13  ω    -47.00 -21.00   0.50  250.00    --  -90.00  38.00  90.00   52
 14  ω     40.00  86.00   0.50  250.00    --  109.41 -77.00 120.00   92
 15  ω    118.00 178.00   0.50  250.00    --  109.41 125.00 -60.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0178223000
_diffrn_orient_matrix_UB_12      0.0830106000
_diffrn_orient_matrix_UB_13      -0.0107301000
_diffrn_orient_matrix_UB_21      -0.1361026000
_diffrn_orient_matrix_UB_22      0.0090532000
_diffrn_orient_matrix_UB_23      0.0429409000
_diffrn_orient_matrix_UB_31      0.1736478000
_diffrn_orient_matrix_UB_32      0.0154327000
_diffrn_orient_matrix_UB_33      0.0325313000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2102
_reflns_number_total             3325
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      0.996
_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)+(0.0945P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1645
_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
O2 O 0.3429(3) 0.58462(10) 0.65993(7) 0.0303(5) Uani 1 1 d . . . . .
O6 O 0.6668(4) 0.96873(12) 0.78466(7) 0.0374(6) Uani 1 1 d . . . . .
O1 O 0.2944(4) 0.71157(11) 0.52135(7) 0.0384(6) Uani 1 1 d . . . . .
O4 O 0.4593(3) 0.68989(11) 0.71204(7) 0.0371(6) Uani 1 1 d . . . . .
O3 O 0.3958(3) 0.77035(11) 0.65321(7) 0.0369(6) Uani 1 1 d . . . . .
O5 O 0.4806(4) 0.89937(12) 0.83264(7) 0.0420(6) Uani 1 1 d . . . . .
N4 N 0.2554(3) 0.44919(12) 0.52435(8) 0.0234(5) Uani 1 1 d . . . . .
N3 N 0.2989(4) 0.51600(12) 0.59364(8) 0.0252(6) Uani 1 1 d . . . . .
N1 N 0.2431(3) 0.57891(12) 0.47021(8) 0.0257(6) Uani 1 1 d . . . . .
N2 N 0.3188(4) 0.64596(13) 0.58985(8) 0.0263(6) Uani 1 1 d . . . . .
N5 N 0.1674(4) 0.30855(13) 0.38069(8) 0.0285(6) Uani 1 1 d . . . . .
C10 C 0.2219(4) 0.51318(15) 0.44940(9) 0.0238(6) Uani 1 1 d . . . . .
C4 C 0.2754(4) 0.51608(14) 0.54635(9) 0.0227(6) Uani 1 1 d . . . . .
C1 C 0.2700(4) 0.58016(15) 0.51751(9) 0.0231(6) Uani 1 1 d . . . . .
C5 C 0.2291(4) 0.44533(16) 0.47533(9) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.2941(4) 0.65198(15) 0.54107(10) 0.0268(6) Uani 1 1 d . . . . .
C6 C 0.2089(4) 0.37902(16) 0.45147(11) 0.0257(6) Uani 1 1 d . . . . .
C9 C 0.1960(4) 0.50897(16) 0.39944(10) 0.0270(6) Uani 1 1 d . . . . .
C3 C 0.3200(4) 0.58096(14) 0.61510(9) 0.0239(6) Uani 1 1 d . . . . .
C7 C 0.1817(4) 0.37612(15) 0.40169(10) 0.0236(6) Uani 1 1 d . . . . .
C15 C 0.4496(4) 0.75581(16) 0.69318(10) 0.0289(7) Uani 1 1 d . . . . .
C8 C 0.1767(4) 0.44470(15) 0.37472(10) 0.0261(6) Uani 1 1 d . . . . .
C17 C 0.5431(5) 0.85866(16) 0.75592(10) 0.0299(7) Uani 1 1 d . . . . .
C18 C 0.5605(5) 0.91088(16) 0.79537(10) 0.0299(7) Uani 1 1 d . . . . .
C16 C 0.5100(4) 0.81263(16) 0.72674(10) 0.0301(7) Uani 1 1 d . . . . .
C11 C 0.2595(6) 0.38073(16) 0.55241(11) 0.0307(7) Uani 1 1 d . . . . .
C14 C 0.1685(6) 0.44965(18) 0.32099(11) 0.0320(7) Uani 1 1 d . . . . .
C12 C 0.2079(6) 0.24214(17) 0.40856(11) 0.0347(8) Uani 1 1 d . . . . .
C13 C 0.0643(5) 0.29404(19) 0.33602(11) 0.0340(8) Uani 1 1 d . . . . .
H14A H 0.041(5) 0.4449(17) 0.3097(11) 0.026(8) Uiso 1 1 d . . . . .
H12A H 0.330(6) 0.245(2) 0.4275(12) 0.045(10) Uiso 1 1 d . . . . .
H12B H 0.221(5) 0.201(2) 0.3868(12) 0.039(9) Uiso 1 1 d . . . . .
H12C H 0.112(5) 0.2294(18) 0.4302(11) 0.031(9) Uiso 1 1 d . . . . .
H13A H 0.156(5) 0.2864(18) 0.3065(12) 0.038(9) Uiso 1 1 d . . . . .
H13B H -0.037(5) 0.332(2) 0.3291(11) 0.037(9) Uiso 1 1 d . . . . .
H14B H 0.241(5) 0.4117(19) 0.3030(12) 0.037(9) Uiso 1 1 d . . . . .
H9 H 0.195(5) 0.5549(19) 0.3779(11) 0.037(9) Uiso 1 1 d . . . . .
H11A H 0.131(5) 0.3548(19) 0.5509(11) 0.035(9) Uiso 1 1 d . . . . .
H11B H 0.369(5) 0.353(2) 0.5394(12) 0.044(10) Uiso 1 1 d . . . . .
H6 H 0.212(4) 0.3397(18) 0.4687(11) 0.027(8) Uiso 1 1 d . . . . .
H14C H 0.214(6) 0.502(3) 0.3099(14) 0.065(12) Uiso 1 1 d . . . . .
H2 H 0.335(5) 0.686(2) 0.6070(13) 0.050(11) Uiso 1 1 d . . . . .
H11C H 0.289(5) 0.394(2) 0.5846(13) 0.043(10) Uiso 1 1 d . . . . .
H13C H -0.009(6) 0.254(3) 0.3400(14) 0.059(12) Uiso 1 1 d . . . . .
H6A H 0.669(6) 1.005(3) 0.8095(15) 0.064(12) Uiso 1 1 d . . . . .
H4 H 0.395(7) 0.655(3) 0.6872(17) 0.085(15) 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
O2 C3 1.269(3) . ?
O6 C18 1.319(4) . ?
O6 H6A 0.96(5) . ?
O1 C2 1.215(3) . ?
O4 C15 1.310(3) . ?
O4 H4 1.05(5) . ?
O3 C15 1.211(3) . ?
O5 C18 1.202(3) . ?
N4 C4 1.369(3) . ?
N4 C5 1.388(3) . ?
N4 C11 1.471(4) . ?
N3 C4 1.336(3) . ?
N3 C3 1.332(3) . ?
N1 C10 1.336(3) . ?
N1 C1 1.339(3) . ?
N2 C2 1.383(4) . ?
N2 C3 1.376(3) . ?
N2 H2 0.88(4) . ?
N5 C7 1.364(4) . ?
N5 C12 1.464(4) . ?
N5 C13 1.467(4) . ?
C10 C5 1.431(4) . ?
C10 C9 1.414(4) . ?
C4 C1 1.417(4) . ?
C1 C2 1.471(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.410(4) . ?
C6 H6 0.86(3) . ?
C9 C8 1.363(4) . ?
C9 H9 1.03(3) . ?
C7 C8 1.457(4) . ?
C15 C16 1.458(4) . ?
C8 C14 1.510(4) . ?
C17 C18 1.462(4) . ?
C17 C16 1.192(4) . ?
C11 H11A 1.01(3) . ?
C11 H11B 0.99(4) . ?
C11 H11C 0.96(4) . ?
C14 H14A 0.94(3) . ?
C14 H14B 0.99(4) . ?
C14 H14C 1.05(5) . ?
C12 H12A 1.00(4) . ?
C12 H12B 0.97(4) . ?
C12 H12C 0.93(3) . ?
C13 H13A 1.06(4) . ?
C13 H13B 1.01(4) . ?
C13 H13C 0.90(5) . ?

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
C18 O6 H6A 113(3) . . ?
C15 O4 H4 105(3) . . ?
C4 N4 C5 120.3(2) . . ?
C4 N4 C11 120.4(2) . . ?
C5 N4 C11 119.3(2) . . ?
C3 N3 C4 117.4(2) . . ?
C10 N1 C1 117.6(2) . . ?
C2 N2 H2 119(2) . . ?
C3 N2 C2 125.3(2) . . ?
C3 N2 H2 115(2) . . ?
C7 N5 C12 119.7(2) . . ?
C7 N5 C13 124.4(2) . . ?
C12 N5 C13 113.7(2) . . ?
N1 C10 C5 122.9(2) . . ?
N1 C10 C9 119.7(2) . . ?
C9 C10 C5 117.5(2) . . ?
N4 C4 C1 117.9(2) . . ?
N3 C4 N4 117.3(2) . . ?
N3 C4 C1 124.8(2) . . ?
N1 C1 C4 123.7(2) . . ?
N1 C1 C2 118.4(2) . . ?
C4 C1 C2 117.9(2) . . ?
N4 C5 C10 117.7(2) . . ?
C6 C5 N4 122.4(3) . . ?
C6 C5 C10 119.9(2) . . ?
O1 C2 N2 121.4(3) . . ?
O1 C2 C1 125.8(3) . . ?
N2 C2 C1 112.9(2) . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 H6 116(2) . . ?
C7 C6 H6 122(2) . . ?
C10 C9 H9 122.5(18) . . ?
C8 C9 C10 124.2(3) . . ?
C8 C9 H9 113.2(18) . . ?
O2 C3 N3 120.5(2) . . ?
O2 C3 N2 117.8(2) . . ?
N3 C3 N2 121.7(2) . . ?
N5 C7 C6 118.1(2) . . ?
N5 C7 C8 122.9(2) . . ?
C6 C7 C8 119.0(2) . . ?
O4 C15 C16 111.8(3) . . ?
O3 C15 O4 126.1(3) . . ?
O3 C15 C16 122.2(3) . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 C14 117.4(3) . . ?
C7 C8 C14 124.7(3) . . ?
C16 C17 C18 171.9(3) . . ?
O6 C18 C17 113.0(3) . . ?
O5 C18 O6 126.6(3) . . ?
O5 C18 C17 120.5(3) . . ?
C17 C16 C15 174.1(3) . . ?
N4 C11 H11A 110.6(19) . . ?
N4 C11 H11B 105(2) . . ?
N4 C11 H11C 107(2) . . ?
H11A C11 H11B 115(3) . . ?
H11A C11 H11C 110(3) . . ?
H11B C11 H11C 108(3) . . ?
C8 C14 H14A 111.4(19) . . ?
C8 C14 H14B 116.5(19) . . ?
C8 C14 H14C 110(2) . . ?
H14A C14 H14B 104(3) . . ?
H14A C14 H14C 105(3) . . ?
H14B C14 H14C 109(3) . . ?
N5 C12 H12A 114(2) . . ?
N5 C12 H12B 108(2) . . ?
N5 C12 H12C 114(2) . . ?
H12A C12 H12B 107(3) . . ?
H12A C12 H12C 106(3) . . ?
H12B C12 H12C 107(3) . . ?
N5 C13 H13A 113.5(18) . . ?
N5 C13 H13B 112.6(18) . . ?
N5 C13 H13C 109(3) . . ?
H13A C13 H13B 111(3) . . ?
H13A C13 H13C 110(3) . . ?
H13B C13 H13C 101(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6A O2 0.96(5) 1.68(5) 2.616(3) 164(4) 3_656 yes
O4 H4 O2 1.05(5) 1.53(5) 2.538(3) 161(4) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C4 C1 N1 1.2(4) . . . . ?
N4 C4 C1 C2 -179.2(3) . . . . ?
N4 C5 C6 C7 179.8(3) . . . . ?
N3 C4 C1 N1 -178.8(3) . . . . ?
N3 C4 C1 C2 0.7(4) . . . . ?
N1 C10 C5 N4 1.4(4) . . . . ?
N1 C10 C5 C6 -179.0(3) . . . . ?
N1 C10 C9 C8 178.7(3) . . . . ?
N1 C1 C2 O1 -1.0(5) . . . . ?
N1 C1 C2 N2 179.4(3) . . . . ?
N5 C7 C8 C9 -178.8(3) . . . . ?
N5 C7 C8 C14 -4.1(5) . . . . ?
C10 N1 C1 C4 -0.6(4) . . . . ?
C10 N1 C1 C2 179.9(3) . . . . ?
C10 C5 C6 C7 0.2(4) . . . . ?
C10 C9 C8 C7 0.5(4) . . . . ?
C10 C9 C8 C14 -174.5(3) . . . . ?
C4 N4 C5 C10 -0.7(4) . . . . ?
C4 N4 C5 C6 179.7(3) . . . . ?
C4 N3 C3 O2 -180.0(3) . . . . ?
C4 N3 C3 N2 -0.3(4) . . . . ?
C4 C1 C2 O1 179.4(3) . . . . ?
C4 C1 C2 N2 -0.2(4) . . . . ?
C1 N1 C10 C5 -0.8(4) . . . . ?
C1 N1 C10 C9 -179.1(3) . . . . ?
C5 N4 C4 N3 179.5(2) . . . . ?
C5 N4 C4 C1 -0.5(4) . . . . ?
C5 C10 C9 C8 0.3(4) . . . . ?
C5 C6 C7 N5 178.5(3) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C2 N2 C3 O2 -179.4(3) . . . . ?
C2 N2 C3 N3 0.9(5) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C6 C7 C8 C14 173.6(3) . . . . ?
C9 C10 C5 N4 179.7(2) . . . . ?
C9 C10 C5 C6 -0.7(4) . . . . ?
C3 N3 C4 N4 179.5(3) . . . . ?
C3 N3 C4 C1 -0.5(4) . . . . ?
C3 N2 C2 O1 179.8(3) . . . . ?
C3 N2 C2 C1 -0.6(4) . . . . ?
C11 N4 C4 N3 0.2(4) . . . . ?
C11 N4 C4 C1 -179.9(3) . . . . ?
C11 N4 C5 C10 178.7(3) . . . . ?
C11 N4 C5 C6 -0.9(4) . . . . ?
C12 N5 C7 C6 -8.7(4) . . . . ?
C12 N5 C7 C8 169.0(3) . . . . ?
C13 N5 C7 C6 153.6(3) . . . . ?
C13 N5 C7 C8 -28.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_exptl_crystal_recrystallization_method 
'seeding in acetonitrile after liquid-assisted grinding'
_exptl_crystal_preparation       Luminescent
