# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_5fluorouracil-salicylic-acid-cocrystal
_database_code_depnum_ccdc_archive 'CCDC 1885425'
loop_
_audit_author_name
_audit_author_address
'Xia-Lin Dai'
;Sun Yat-sen University
China
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2017-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C14 H12 O6), 2(C4 H3 F N2 O2)'
_chemical_formula_sum            'C15 H12 F2 N4 O7'
_chemical_formula_weight         398.29
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c '
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.5354(8)
_cell_length_b                   6.9178(4)
_cell_length_c                   15.7237(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.902(5)
_cell_angle_gamma                90
_cell_volume                     1569.61(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      65.1290
_cell_measurement_theta_min      2.7450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6426
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        65.569
_diffrn_reflns_theta_max         65.569
_diffrn_reflns_theta_min         5.669
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -38.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega   13.00   69.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -30.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega    7.00   84.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   84.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega   16.00  121.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -61.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
  7 omega   29.00  174.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218   15.0000 -180.0000 145

#__ type_ start__ end____ width___ exp.time_
  8 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
  9 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
 10 omega -157.00  -53.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
 11 omega -161.00  -52.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -30.0000  -60.0000 109

#__ type_ start__ end____ width___ exp.time_
 12 omega    7.00   84.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 13 omega   57.00  169.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218   77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
 14 omega -120.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  -77.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
 15 omega  -99.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  126.0000   90.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0901159000
_diffrn_orient_matrix_UB_12      0.0372816000
_diffrn_orient_matrix_UB_13      -0.0398274000
_diffrn_orient_matrix_UB_21      0.0543681000
_diffrn_orient_matrix_UB_22      0.0106734000
_diffrn_orient_matrix_UB_23      0.0902294000
_diffrn_orient_matrix_UB_31      0.0179573000
_diffrn_orient_matrix_UB_32      -0.2193760000
_diffrn_orient_matrix_UB_33      -0.0024266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1022
_reflns_number_total             1327
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.627
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0015(3)
_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   0.903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1327
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.139
_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)+(0.1129P)²+3.7038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1806
_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
 O3-C5
 1.2 with sigma of 0.005
 C5-O4
 1.32 with sigma of 0.005
 C6-C10
 1.42 with sigma of 0.005
 C10-C9
 1.42 with sigma of 0.005
 F1-O3_$3
 2.9 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(N2)
Uanis(C9) = Uanis(C21)
4. Others
 Fixed Sof: C10(0.5) H10(0.5) C8(0.5) H8(0.5) C5(0.5) O5(0.5) H5(0.5) O4(0.5)
 H4(0.5) O3(0.5) C6(0.5) C9(0.5) H9(0.5) C21(0.5) H21(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), N2(H2), N1(H1), C2(H2A), C9(H9), C21(H21)
5.b Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4)
;
_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
C10 C 0.491(2) 0.3665(7) 0.7578(12) 0.032(3) Uani 0.5 1 d D . . A -1
H10 H 0.4982 0.2431 0.7361 0.039 Uiso 0.5 1 calc R . . A -1
F1 F 0.61186(16) 0.0049(3) 0.53675(12) 0.0664(7) Uani 1 1 d D . . . .
C8 C 0.4626(4) 0.7354(8) 0.8199(3) 0.0317(12) Uani 0.5 1 d . . . A -1
H8 H 0.4496 0.8584 0.8392 0.038 Uiso 0.5 1 calc R . . A -1
O1 O 0.75011(14) 0.0011(2) 0.23811(13) 0.0356(6) Uani 1 1 d . . . . .
N2 N 0.70279(14) 0.1670(3) 0.34949(13) 0.0302(5) Uani 1 1 d . . . . .
H2 H 0.7170 0.2731 0.3258 0.036 Uiso 1 1 calc R . . . .
O2 O 0.65370(13) 0.3403(3) 0.45851(12) 0.0426(6) Uani 1 1 d . . . . .
N1 N 0.69727(14) -0.1652(3) 0.34647(14) 0.0325(6) Uani 1 1 d . . . . .
H1 H 0.7069 -0.2735 0.3222 0.039 Uiso 1 1 calc R . . . .
C7 C 0.5000 0.7150(5) 0.7500 0.0321(9) Uani 1 2 d S T P . .
C3 C 0.71835(18) 0.0000(3) 0.30730(18) 0.0290(7) Uani 1 1 d . . . . .
C2 C 0.66127(18) -0.1685(4) 0.42311(18) 0.0366(7) Uani 1 1 d . . . . .
H2A H 0.6476 -0.2855 0.4479 0.044 Uiso 1 1 calc R . . . .
C4 C 0.66658(17) 0.1829(4) 0.42625(16) 0.0302(5) Uani 1 1 d . . . . .
C1 C 0.6461(2) -0.0019(4) 0.46174(19) 0.0410(8) Uani 1 1 d . . . . .
C5 C 0.5552(5) 0.5048(6) 0.6318(4) 0.0238(17) Uani 0.5 1 d D . . A -1
O5 O 0.5217(3) 0.8779(5) 0.7024(2) 0.0368(9) Uani 0.5 1 d . . . A -1
H5 H 0.5432 0.8423 0.6590 0.055 Uiso 0.5 1 calc GR . . A -1
O4 O 0.5609(3) 0.3274(5) 0.6046(2) 0.0421(10) Uani 0.5 1 d D . . A -1
H4 H 0.5861 0.3268 0.5607 0.063 Uiso 0.5 1 calc GR . . A -1
O3 O 0.5835(3) 0.6344(5) 0.5937(3) 0.0436(11) Uani 0.5 1 d D . . A -1
C6 C 0.5147(3) 0.5301(7) 0.7121(3) 0.0279(12) Uani 0.5 1 d D . . A -1
C9 C 0.4557(3) 0.3914(10) 0.8369(3) 0.0326(11) Uani 0.5 1 d D . . A -1
H9 H 0.4418 0.2854 0.8694 0.039 Uiso 0.5 1 calc R . . A -1
C21 C 0.4425(7) 0.5784(14) 0.8648(6) 0.0326(11) Uani 0.5 1 d . . . A -1
H21 H 0.4188 0.5960 0.9166 0.039 Uiso 0.5 1 calc R . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C10 H10 0.9300 . ?
C10 C6 1.405(4) . ?
C10 C9 1.411(5) . ?
F1 C1 1.335(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.291(5) . ?
C8 C21 1.347(11) . ?
O1 C3 1.232(3) . ?
N2 H2 0.8600 . ?
N2 C3 1.364(3) . ?
N2 C4 1.378(3) . ?
O2 C4 1.225(3) . ?
N1 H1 0.8600 . ?
N1 C3 1.351(3) . ?
N1 C2 1.370(4) . ?
C7 O5 1.410(5) . ?
C7 C6 1.438(6) . ?
C2 H2A 0.9300 . ?
C2 C1 1.334(4) . ?
C4 C1 1.440(4) . ?
C5 O4 1.305(4) . ?
C5 O3 1.180(5) . ?
C5 C6 1.467(8) . ?
O5 H5 0.8200 . ?
O4 H4 0.8200 . ?
C9 H9 0.9300 . ?
C9 C21 1.386(11) . ?
C21 H21 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
C6 C10 H10 120.4 . . ?
C6 C10 C9 119.3(5) . . ?
C9 C10 H10 120.4 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C21 119.9(6) . . ?
C21 C8 H8 120.1 . . ?
C3 N2 H2 116.7 . . ?
C3 N2 C4 126.7(2) . . ?
C4 N2 H2 116.7 . . ?
C3 N1 H1 118.4 . . ?
C3 N1 C2 123.1(2) . . ?
C2 N1 H1 118.4 . . ?
C8 C7 O5 120.6(4) . . ?
C8 C7 C6 123.3(4) . . ?
O5 C7 C6 115.9(2) . . ?
O1 C3 N2 121.7(2) . . ?
O1 C3 N1 122.5(2) . . ?
N1 C3 N2 115.8(2) . . ?
N1 C2 H2A 120.4 . . ?
C1 C2 N1 119.2(2) . . ?
C1 C2 H2A 120.4 . . ?
N2 C4 C1 112.7(2) . . ?
O2 C4 N2 121.8(2) . . ?
O2 C4 C1 125.4(2) . . ?
F1 C1 C4 115.3(3) . . ?
C2 C1 F1 122.2(3) . . ?
C2 C1 C4 122.5(3) . . ?
O4 C5 C6 116.2(5) . . ?
O3 C5 O4 120.5(5) . . ?
O3 C5 C6 123.2(5) . . ?
C7 O5 H5 109.5 . . ?
C5 O4 H4 109.5 . . ?
C10 C6 C7 116.6(4) . . ?
C5 C6 C10 119.5(5) . . ?
C5 C6 C7 123.9(4) . . ?
C10 C9 H9 120.9 . . ?
C21 C9 C10 118.2(6) . . ?
C21 C9 H9 120.9 . . ?
C8 C21 H21 118.7 . . ?
C9 C21 C8 122.6(7) . . ?
C9 C21 H21 118.7 . . ?

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
N2 H2 O1 0.86 1.96 2.817(3) 174.7 4_655
N1 H1 O1 0.86 1.97 2.815(3) 169.6 4_645
O5 H5 O3 0.82 1.90 2.633(6) 148.1 .
O4 H4 O2 0.82 1.98 2.802(4) 175.7 .

_olex2_submission_special_instructions 'No special instructions were received'
