# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mcg1937
_database_code_depnum_ccdc_archive 'CCDC 2050223'
loop_
_audit_author_name
_audit_author_address
'Dale C. Swenson'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            4(5-fu).(bpe)
_chemical_name_systematic        
'5-fluoro-1H,3H-pyrimidine-2,4-dione, 1,2-bis(4-pyridyl)ethylene'
_chemical_formula_moiety         '4(C4 H3 F N2 O2), C12 H10 N2'
_chemical_formula_sum            'C28 H22 F4 N10 O8'
_chemical_formula_weight         702.55
_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 0.0033 0.0016 '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 0.0171 0.0103 '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'

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

_cell_length_a                   9.1087(9)
_cell_length_b                   10.9966(11)
_cell_length_c                   14.9346(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.732(5)
_cell_angle_gamma                90
_cell_volume                     1492.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      1
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale orangish yellow'
_exptl_crystal_colour_lustre     pale
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.9941
_exptl_transmission_factor_min   0.9602
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8833
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_min         2.907
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker Nonius Kappa CCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2358
_reflns_number_total             3110
_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       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.050
_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)+(0.0612P)²+0.1987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), N009(H009), N00A(H00A), C00E(H00E), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.37004(10) 0.25705(8) 0.75997(7) 0.0579(3) Uani 1 1 d . . . . .
O002 O 0.40519(11) 0.78531(8) 0.64887(7) 0.0468(3) Uani 1 1 d . . . . .
O003 O 0.11430(11) 0.60920(8) 0.54881(7) 0.0452(3) Uani 1 1 d . . . . .
F004 F 0.17120(13) 1.13022(9) 0.42239(7) 0.0712(3) Uani 1 1 d . . . . .
O005 O 0.11745(12) 0.21326(8) 0.63815(8) 0.0513(3) Uani 1 1 d . . . . .
O006 O 0.41646(13) 1.17513(9) 0.54844(8) 0.0539(3) Uani 1 1 d . . . . .
N007 N 0.40416(13) 0.98151(9) 0.60036(8) 0.0377(3) Uani 1 1 d . . . . .
H007 H 0.473721 0.997532 0.640336 0.045 Uiso 1 1 calc R . . . .
N008 N 0.28553(12) 0.55105(10) 0.66446(8) 0.0380(3) Uani 1 1 d . . . . .
H008 H 0.316420 0.624535 0.671581 0.046 Uiso 1 1 calc R . . . .
N009 N 0.12097(13) 0.41154(9) 0.59401(8) 0.0386(3) Uani 1 1 d . . . . .
H009 H 0.049840 0.396757 0.554807 0.046 Uiso 1 1 calc R . . . .
N00A N 0.23068(13) 0.84409(10) 0.53479(8) 0.0431(3) Uani 1 1 d . . . . .
H00A H 0.192533 0.772529 0.532507 0.052 Uiso 1 1 calc R . . . .
N00B N 0.62664(14) 0.99790(11) 0.75238(9) 0.0479(3) Uani 1 1 d . . . . .
C00C C 0.84883(15) 0.97321(11) 0.89981(9) 0.0359(3) Uani 1 1 d . . . . .
C00D C 0.34989(15) 0.86488(12) 0.59754(9) 0.0369(3) Uani 1 1 d . . . . .
C00E C 0.96599(15) 0.95610(12) 0.97536(9) 0.0380(3) Uani 1 1 d . . . . .
H00E H 0.993662 0.876487 0.989007 0.046 Uiso 1 1 calc R . . . .
C00F C 0.17134(15) 0.52887(11) 0.59994(9) 0.0351(3) Uani 1 1 d . . . . .
C00G C 0.17514(16) 0.31368(11) 0.64615(10) 0.0384(3) Uani 1 1 d . . . . .
C00H C 0.35549(16) 1.07604(12) 0.54359(10) 0.0395(3) Uani 1 1 d . . . . .
C00I C 0.30307(16) 0.34685(13) 0.70897(10) 0.0398(3) Uani 1 1 d . . . . .
C00J C 0.67690(18) 1.09327(13) 0.80285(11) 0.0493(4) Uani 1 1 d . . . . .
H00J H 0.637247 1.169440 0.789024 0.059 Uiso 1 1 calc R . . . .
C00K C 0.79529(16) 0.87401(13) 0.84824(10) 0.0430(4) Uani 1 1 d . . . . .
H00K H 0.831684 0.796532 0.861212 0.052 Uiso 1 1 calc R . . . .
C00L C 0.35220(16) 0.46066(12) 0.71797(10) 0.0401(3) Uani 1 1 d . . . . .
H00L H 0.429717 0.479261 0.759323 0.048 Uiso 1 1 calc R . . . .
C00M C 0.78589(16) 1.08587(13) 0.87551(11) 0.0446(4) Uani 1 1 d . . . . .
H00M H 0.815322 1.155746 0.906847 0.053 Uiso 1 1 calc R . . . .
C00N C 0.68668(17) 0.88985(14) 0.77671(11) 0.0480(4) Uani 1 1 d . . . . .
H00N H 0.654865 0.821300 0.744536 0.058 Uiso 1 1 calc R . . . .
C00O C 0.17058(17) 0.93162(13) 0.47629(10) 0.0455(4) Uani 1 1 d . . . . .
H00O H 0.091617 0.913263 0.435934 0.055 Uiso 1 1 calc R . . . .
C00P C 0.22918(17) 1.04266(12) 0.47957(10) 0.0446(4) 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
F001 C00I 1.3663(16) . ?
O002 C00D 1.2477(16) . ?
O003 C00F 1.2577(16) . ?
F004 C00P 1.3699(16) . ?
O005 C00G 1.2255(16) . ?
O006 C00H 1.2230(16) . ?
N007 C00D 1.3741(16) . ?
N007 C00H 1.3954(17) . ?
N008 C00F 1.3926(18) . ?
N008 C00L 1.3901(17) . ?
N009 C00F 1.3703(16) . ?
N009 C00G 1.3993(17) . ?
N00A C00D 1.4061(18) . ?
N00A C00O 1.3883(18) . ?
N00B C00J 1.3537(19) . ?
N00B C00N 1.3479(19) . ?
C00C C00E 1.513(2) . ?
C00C C00K 1.4044(19) . ?
C00C C00M 1.4029(19) . ?
C00E C00E 1.341(3) 3_777 ?
C00G C00I 1.493(2) . ?
C00H C00P 1.493(2) . ?
C00I C00L 1.333(2) . ?
C00J C00M 1.425(2) . ?
C00K C00N 1.419(2) . ?
C00O C00P 1.332(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
C00D N007 C00H 125.25(12) . . ?
C00L N008 C00F 123.45(11) . . ?
C00F N009 C00G 125.71(12) . . ?
C00O N00A C00D 124.22(11) . . ?
C00N N00B C00J 114.60(12) . . ?
C00K C00C C00E 121.01(12) . . ?
C00M C00C C00E 123.99(12) . . ?
C00M C00C C00K 115.00(12) . . ?
O002 C00D N007 120.37(12) . . ?
O002 C00D N00A 123.97(12) . . ?
N007 C00D N00A 115.65(12) . . ?
C00E C00E C00C 126.72(16) 3_777 . ?
O003 C00F N008 123.89(11) . . ?
O003 C00F N009 119.91(12) . . ?
N009 C00F N008 116.20(12) . . ?
O005 C00G N009 120.35(13) . . ?
O005 C00G C00I 126.42(12) . . ?
N009 C00G C00I 113.23(11) . . ?
O006 C00H N007 120.17(14) . . ?
O006 C00H C00P 125.81(13) . . ?
N007 C00H C00P 114.02(11) . . ?
F001 C00I C00G 118.40(12) . . ?
C00L C00I F001 119.18(13) . . ?
C00L C00I C00G 122.41(13) . . ?
N00B C00J C00M 124.99(13) . . ?
C00C C00K C00N 121.19(13) . . ?
C00I C00L N008 118.82(13) . . ?
C00C C00M C00J 120.02(13) . . ?
N00B C00N C00K 124.19(13) . . ?
C00P C00O N00A 118.14(14) . . ?
F004 C00P C00H 118.43(12) . . ?
C00O C00P F004 118.95(14) . . ?
C00O C00P C00H 122.62(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_mcg18177
_database_code_depnum_ccdc_archive 'CCDC 2050224'
loop_
_audit_author_name
_audit_author_address
'Dale C. Swenson'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            (resv).(bpe).(5-fu)
_chemical_name_systematic        
"3,5,4'-trihydroxy-trans-stilbene, 1,2-bis(4-pyridyl)ethylene, 5-fluoro-1H,3H-pyrimidine-2,4-dione"
_chemical_formula_moiety         'C4 H3 F N2 O2, C14 H12 O3, C12 H10 N2'
_chemical_formula_sum            'C30 H25 F N4 O5'
_chemical_formula_weight         540.54
_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 0.0033 0.0016 '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 0.0171 0.0103 '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'

_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                   9.4819(9)
_cell_length_b                   10.6517(11)
_cell_length_c                   13.5060(14)
_cell_angle_alpha                76.407(5)
_cell_angle_beta                 85.696(5)
_cell_angle_gamma                88.382(5)
_cell_volume                     1322.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4772
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.9925
_exptl_transmission_factor_min   0.9227
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7558
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.967
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2073
_reflns_number_total             4645
_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       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      0.969
_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)+(0.0777P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C7A) = Uanis(C7B)
Uanis(C6B) = Uanis(C6A)
4. Same fragment restrains
{C6B, C7B} sigma for 1-2: 0.02, 1-3: 0.04
{C6A, C6B} sigma for 1-2: 0.02, 1-3: 0.04
as
{C6A, C7A}
5. Others
 Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=1-FVAR(1)
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3A), N4(H4A), C17(H17), C15(H15), C20(H20), C23(H23), C13(H13), C26(H26),
 C22(H22), C19(H19), C28(H28), C25(H25), C10(H10), C11(H11), C12(H12), C5(H5),
 C9(H9), C4(H4), C6A(H6A), C7A(H7A), C6B(H6B), C7B(H7B), C2(H2A), C1(H1A)
6.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.3442(2) 1.20912(16) 0.34192(15) 0.0857(6) Uani 1 1 d . . . . .
O4 O 0.0812(2) 1.33771(18) 0.53569(16) 0.0673(7) Uani 1 1 d . . . . .
O5 O -0.1438(2) 1.02871(18) 0.42597(16) 0.0705(7) Uani 1 1 d . . . . .
O2 O 1.1486(2) 0.67694(19) 0.8745(2) 0.0844(8) Uani 1 1 d . . . . .
H2 H 1.195655 0.610156 0.888708 0.127 Uiso 1 1 calc GR . . . .
O3 O 0.3610(2) 1.37902(19) 0.5596(2) 0.0986(9) Uani 1 1 d . . . . .
H3 H 0.290914 1.351300 0.540027 0.148 Uiso 1 1 calc GR . . . .
N3 N -0.0369(2) 1.1834(2) 0.48376(18) 0.0565(7) Uani 1 1 d . . . . .
H3A H 0.022122 1.125927 0.512405 0.068 Uiso 1 1 calc R . . . .
N4 N -0.1188(3) 1.3927(2) 0.45314(19) 0.0609(7) Uani 1 1 d . . . . .
H4A H -0.114513 1.470892 0.459725 0.073 Uiso 1 1 calc R . . . .
O1 O 0.8536(3) 0.4004(2) 0.7490(2) 0.0977(9) Uani 1 1 d . . . . .
H1 H 0.909293 0.345682 0.777299 0.146 Uiso 1 1 calc GR . . . .
N2 N 1.0312(3) 0.2073(2) 0.8425(3) 0.0785(9) Uani 1 1 d . . . . .
C21 C 0.6461(3) 1.0791(3) 0.6576(2) 0.0552(8) Uani 1 1 d . . . . .
N1 N 1.6830(3) -0.4567(3) 1.0779(3) 0.0835(9) Uani 1 1 d . . . . .
C16 C 0.8333(3) 0.7451(3) 0.7343(2) 0.0547(8) Uani 1 1 d . . . . .
C27 C -0.0179(3) 1.3072(3) 0.4932(2) 0.0559(8) Uani 1 1 d . . . . .
C17 C 0.8035(3) 0.6231(3) 0.7222(2) 0.0637(9) Uani 1 1 d . . . . .
H17 H 0.726237 0.611807 0.686829 0.076 Uiso 1 1 calc R . . . .
C24 C 0.4547(3) 1.2794(3) 0.5903(3) 0.0659(9) Uani 1 1 d . . . . .
C15 C 0.9498(3) 0.7607(3) 0.7860(2) 0.0578(9) Uani 1 1 d . . . . .
H15 H 0.971447 0.842275 0.793897 0.069 Uiso 1 1 calc R . . . .
C20 C 0.7459(3) 0.9748(3) 0.6955(2) 0.0618(9) Uani 1 1 d . . . . .
H20 H 0.823731 0.997367 0.725345 0.074 Uiso 1 1 calc R . . . .
C14 C 1.0339(3) 0.6561(3) 0.8258(2) 0.0584(9) Uani 1 1 d . . . . .
C29 C -0.2384(3) 1.2414(3) 0.3922(2) 0.0578(9) Uani 1 1 d . . . . .
C30 C -0.1405(3) 1.1412(3) 0.4333(2) 0.0565(8) Uani 1 1 d . . . . .
C23 C 0.5770(3) 1.3038(3) 0.6294(3) 0.0699(10) Uani 1 1 d . . . . .
H23 H 0.596921 1.387580 0.632934 0.084 Uiso 1 1 calc R . . . .
C13 C 1.0031(3) 0.5340(3) 0.8144(2) 0.0605(9) Uani 1 1 d . . . . .
H13 H 1.059808 0.463455 0.841563 0.073 Uiso 1 1 calc R . . . .
C26 C 0.5219(3) 1.0584(3) 0.6159(3) 0.0710(10) Uani 1 1 d . . . . .
H26 H 0.502168 0.975432 0.610282 0.085 Uiso 1 1 calc R . . . .
C22 C 0.6710(3) 1.2049(3) 0.6637(2) 0.0655(9) Uani 1 1 d . . . . .
H22 H 0.752790 1.222687 0.691518 0.079 Uiso 1 1 calc R . . . .
C19 C 0.7384(3) 0.8529(3) 0.6922(2) 0.0632(9) Uani 1 1 d . . . . .
H19 H 0.663220 0.831977 0.658909 0.076 Uiso 1 1 calc R . . . .
C28 C -0.2270(3) 1.3607(3) 0.4028(2) 0.0636(9) Uani 1 1 d . . . . .
H28 H -0.293020 1.423239 0.375925 0.076 Uiso 1 1 calc R . . . .
C18 C 0.8880(3) 0.5180(3) 0.7623(2) 0.0644(9) Uani 1 1 d . . . . .
C25 C 0.4272(3) 1.1561(3) 0.5826(3) 0.0720(10) Uani 1 1 d . . . . .
H25 H 0.344886 1.139047 0.555002 0.086 Uiso 1 1 calc R . . . .
C10 C 1.0596(4) 0.1858(3) 0.9394(3) 0.0860(12) Uani 1 1 d . . . . .
H10 H 1.011984 0.235214 0.979911 0.103 Uiso 1 1 calc R . . . .
C8 C 1.2260(4) 0.0187(3) 0.9281(4) 0.0797(11) Uani 1 1 d . . . . .
C11 C 1.1014(4) 0.1346(3) 0.7869(3) 0.0858(12) Uani 1 1 d . . . . .
H11 H 1.084597 0.148628 0.718158 0.103 Uiso 1 1 calc R . . . .
C12 C 1.1977(4) 0.0396(3) 0.8260(4) 0.0898(12) Uani 1 1 d . . . . .
H12 H 1.243059 -0.009771 0.784548 0.108 Uiso 1 1 calc R . . . .
C3 C 1.4966(4) -0.2578(3) 0.9970(4) 0.0816(11) Uani 1 1 d . . . . .
C5 C 1.6658(4) -0.4191(4) 0.9806(4) 0.0876(12) Uani 1 1 d . . . . .
H5 H 1.719359 -0.460532 0.936967 0.105 Uiso 1 1 calc R . . . .
C9 C 1.1547(4) 0.0953(4) 0.9834(3) 0.0887(12) Uani 1 1 d . . . . .
H9 H 1.171088 0.085630 1.051855 0.106 Uiso 1 1 calc R . . . .
C4 C 1.5747(4) -0.3228(4) 0.9376(3) 0.0951(12) Uani 1 1 d . . . . .
H4 H 1.566764 -0.302431 0.867437 0.114 Uiso 1 1 calc R . . . .
C6A C 1.3981(5) -0.1570(5) 0.9420(4) 0.0700(15) Uani 0.771(5) 1 d D . P A 1
H6A H 1.391022 -0.149694 0.872591 0.084 Uiso 0.771(5) 1 calc R . P A 1
C7A C 1.3222(5) -0.0797(5) 0.9858(5) 0.0718(16) Uani 0.771(5) 1 d D . P A 1
H7A H 1.328143 -0.085906 1.055177 0.086 Uiso 0.771(5) 1 calc R . P A 1
C6B C 1.3910(19) -0.1474(18) 1.0074(11) 0.0700(15) Uani 0.229(5) 1 d D . P A 2
H6B H 1.363852 -0.126482 1.069237 0.084 Uiso 0.229(5) 1 calc R . P A 2
C7B C 1.344(2) -0.0873(19) 0.9211(11) 0.0718(16) Uani 0.229(5) 1 d D . P A 2
H7B H 1.378103 -0.105050 0.859314 0.086 Uiso 0.229(5) 1 calc R . P A 2
C2 C 1.5133(5) -0.2932(4) 1.0986(4) 0.1143(15) Uani 1 1 d . . . . .
H2A H 1.462281 -0.251215 1.143048 0.137 Uiso 1 1 calc R . . . .
C1 C 1.6074(5) -0.3927(5) 1.1360(3) 0.1200(16) Uani 1 1 d . . . . .
H1A H 1.617486 -0.415207 1.205920 0.144 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C29 1.348(3) . ?
O4 C27 1.226(3) . ?
O5 C30 1.227(3) . ?
O2 H2 0.8200 . ?
O2 C14 1.362(3) . ?
O3 H3 0.8200 . ?
O3 C24 1.372(3) . ?
N3 H3A 0.8600 . ?
N3 C27 1.372(3) . ?
N3 C30 1.378(3) . ?
N4 H4A 0.8600 . ?
N4 C27 1.355(3) . ?
N4 C28 1.365(3) . ?
O1 H1 0.8200 . ?
O1 C18 1.359(3) . ?
N2 C10 1.322(4) . ?
N2 C11 1.333(4) . ?
C21 C20 1.463(4) . ?
C21 C26 1.387(4) . ?
C21 C22 1.390(4) . ?
N1 C5 1.302(4) . ?
N1 C1 1.316(5) . ?
C16 C17 1.386(4) . ?
C16 C15 1.384(4) . ?
C16 C19 1.470(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(4) . ?
C24 C23 1.366(4) . ?
C24 C25 1.375(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.378(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.314(4) . ?
C14 C13 1.387(4) . ?
C29 C30 1.433(4) . ?
C29 C28 1.320(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.378(4) . ?
C13 H13 0.9300 . ?
C13 C18 1.377(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.370(4) . ?
C22 H22 0.9300 . ?
C19 H19 0.9300 . ?
C28 H28 0.9300 . ?
C25 H25 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.363(4) . ?
C8 C12 1.389(5) . ?
C8 C9 1.364(5) . ?
C8 C7A 1.485(6) . ?
C8 C7B 1.58(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9300 . ?
C3 C4 1.347(5) . ?
C3 C6A 1.500(6) . ?
C3 C6B 1.55(2) . ?
C3 C2 1.354(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.371(5) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.295(5) . ?
C7A H7A 0.9300 . ?
C6B H6B 0.9300 . ?
C6B C7B 1.294(5) . ?
C7B H7B 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C1 1.392(5) . ?
C1 H1A 0.9300 . ?

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
C14 O2 H2 109.5 . . ?
C24 O3 H3 109.5 . . ?
C27 N3 H3A 116.5 . . ?
C27 N3 C30 127.0(3) . . ?
C30 N3 H3A 116.5 . . ?
C27 N4 H4A 118.5 . . ?
C27 N4 C28 123.0(2) . . ?
C28 N4 H4A 118.5 . . ?
C18 O1 H1 109.5 . . ?
C10 N2 C11 116.4(3) . . ?
C26 C21 C20 122.6(3) . . ?
C26 C21 C22 116.6(3) . . ?
C22 C21 C20 120.8(3) . . ?
C5 N1 C1 115.1(3) . . ?
C17 C16 C19 118.4(3) . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 C19 122.6(3) . . ?
O4 C27 N3 122.9(3) . . ?
O4 C27 N4 122.6(3) . . ?
N4 C27 N3 114.5(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
O3 C24 C25 121.2(3) . . ?
C23 C24 O3 119.0(3) . . ?
C23 C24 C25 119.8(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C21 C20 H20 116.3 . . ?
C19 C20 C21 127.5(3) . . ?
C19 C20 H20 116.3 . . ?
O2 C14 C15 118.1(3) . . ?
O2 C14 C13 121.4(3) . . ?
C15 C14 C13 120.5(3) . . ?
F1 C29 C30 117.2(3) . . ?
C28 C29 F1 120.8(3) . . ?
C28 C29 C30 122.0(3) . . ?
O5 C30 N3 121.4(3) . . ?
O5 C30 C29 125.7(3) . . ?
N3 C30 C29 112.9(3) . . ?
C24 C23 H23 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C14 C13 H13 120.3 . . ?
C18 C13 C14 119.4(3) . . ?
C18 C13 H13 120.3 . . ?
C21 C26 H26 118.9 . . ?
C25 C26 C21 122.3(3) . . ?
C25 C26 H26 118.9 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C16 C19 H19 115.7 . . ?
C20 C19 C16 128.5(3) . . ?
C20 C19 H19 115.7 . . ?
N4 C28 H28 119.8 . . ?
C29 C28 N4 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
O1 C18 C17 118.2(3) . . ?
O1 C18 C13 121.6(3) . . ?
C13 C18 C17 120.1(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
N2 C10 H10 118.1 . . ?
N2 C10 C9 123.7(4) . . ?
C9 C10 H10 118.1 . . ?
C12 C8 C7A 127.9(4) . . ?
C12 C8 C7B 94.2(6) . . ?
C9 C8 C12 116.6(3) . . ?
C9 C8 C7A 115.5(4) . . ?
C9 C8 C7B 149.0(6) . . ?
N2 C11 H11 118.3 . . ?
N2 C11 C12 123.4(4) . . ?
C12 C11 H11 118.3 . . ?
C8 C12 H12 120.4 . . ?
C11 C12 C8 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C4 C3 C6A 115.3(4) . . ?
C4 C3 C6B 149.7(6) . . ?
C4 C3 C2 116.7(4) . . ?
C2 C3 C6A 128.0(4) . . ?
C2 C3 C6B 93.5(6) . . ?
N1 C5 H5 117.6 . . ?
N1 C5 C4 124.9(4) . . ?
C4 C5 H5 117.6 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C6A H6A 118.1 . . ?
C7A C6A C3 123.7(6) . . ?
C7A C6A H6A 118.1 . . ?
C8 C7A H7A 119.1 . . ?
C6A C7A C8 121.8(6) . . ?
C6A C7A H7A 119.1 . . ?
C3 C6B H6B 123.5 . . ?
C7B C6B C3 113.0(18) . . ?
C7B C6B H6B 123.5 . . ?
C8 C7B H7B 122.4 . . ?
C6B C7B C8 115.3(18) . . ?
C6B C7B H7B 122.4 . . ?
C3 C2 H2A 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C1 C2 H2A 120.2 . . ?
N1 C1 C2 123.7(4) . . ?
N1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
