# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ECB-PRL
_database_code_depnum_ccdc_archive 'CCDC 2410452'
loop_
_audit_author_name
_audit_author_address
'Palash Sanphui'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2024-12-16 deposited with the CCDC.	2025-05-14 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_ECB-PRL             
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01325 Ang. 
RESPONSE: This crystal structure has been solved and refined with 
the use of laboratory powder diffraction data.
;
# end Validation Reply Form

_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        Emtricitabine-proline
_chemical_name_common            Emtricitabine-proline
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 F N3 O3 S, C5 H9 N O2'
_chemical_formula_sum            'C13 H19 F N4 O5 S'
_chemical_formula_weight         362.38
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 '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'
O O 0.0492 0.0322 '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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.1647(6)
_cell_length_b                   25.1972(18)
_cell_length_c                   12.3411(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1606.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    642
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      39.98

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              15 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              1 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              1 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 
thin layer on the non-diffracting silicon plate
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet # options are 'cylinder',
# 'flat_sheet' or 'irregular'

_pd_char_particle_morphology     ?
_pd_char_colour                  colorless # use ICDD colour descriptions

# The following three fields describe the preparation of the specimen. 
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.



_pd_prep_cool_rate               ?
_pd_prep_pressure                101
_pd_prep_temperature             295(2)


_exptl_special_details           
; 
 ? 
;

# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
;
Dept. of Chemistry, Moscow State University, 119234 Moscow, Russia
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Fine focus X-ray tube'
_diffrn_source_target            Cu

_diffrn_radiation_source         'line-focus sealed tube'
_diffrn_radiation_monochromator  'Curved Germanium (111)'
_diffrn_measurement_device       'Stoe Stadi-P'
_diffrn_detector_type            'linear position detector'



_diffrn_reflns_number            ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?


_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;
# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_type           CuK\a~1~
_diffrn_radiation_wavelength     1.54059

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        7501
_pd_meas_2theta_range_min        5.00
_pd_meas_2theta_range_max        80.00
_pd_meas_2theta_range_inc        0.01

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

# The following fields are used to identify the programs used.

_computing_data_collection       ?
_computing_cell_refinement       'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_data_reduction        ?
_computing_structure_solution    'simulated annealing (Zhukov et al., 2001)'
_computing_structure_refinement  MRIA
_computing_molecular_graphics    ?
_computing_publication_material  'MRIA, SHELXL97 (Sheldrick, 2008)'

#==============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text
_pd_proc_ls_profile_function     'split-type pseudo-Voigt (Toraya, 1986)'
_pd_proc_ls_pref_orient_corr     
; 
March-Dollase texture correction (Dollase, 1986),
direction of preferred orientation [100],
texture parameter r = 0.93(1).
;
_pd_proc_ls_background_function  'Chebyshev polynomial up to the 5th order'

_pd_proc_ls_prof_R_factor        0.0371
_pd_proc_ls_prof_wR_factor       0.0489
_pd_proc_ls_prof_wR_expected     0.0179

_refine_special_details          
; 
Two-phase Rietveld refinement was used because the
powder sample contained 6% of the pure Emtricitabine
with the known crystal structure, CCDC refcodes HAKJIM & OMABUC.
;

_refine_ls_R_I_factor            0.065
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     150
_refine_ls_number_restraints     74
_refine_ls_number_constraints    0

# The following item is the same as CHI, the square root of 'CHI squared = 6.219'
_refine_ls_goodness_of_fit_all   2.494

_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .003
_refine_ls_shift/su_mean         .001


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.
_pd_proc_2theta_range_min        5.00
_pd_proc_2theta_range_max        80.00
_pd_proc_2theta_range_inc        0.01

_pd_proc_wavelength              1.54059

_pd_block_diffractogram_id       ECB-PRL_pattern # The id used for the block
# containing the powder 
# pattern profile (section 11).

# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   none
_pd_proc_info_data_reduction     ?

#==============================================================================

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.8752(8) 0.32690(10) 0.5071(2) 0.0680(15) Uiso 1 1 d . . .
F1 F 0.4590(12) 0.41321(19) 0.8827(4) 0.071(3) Uiso 1 1 d . . .
O1 O 0.6475(13) 0.5038(2) 0.5023(5) 0.070(3) Uiso 1 1 d . . .
O2 O 1.1464(14) 0.3931(2) 0.6163(5) 0.075(3) Uiso 1 1 d . . .
O3 O 1.0578(15) 0.3030(2) 0.7474(6) 0.065(3) Uiso 1 1 d . . .
H3 H 1.0242 0.2716 0.7609 0.098 Uiso 1 1 calc . . .
N1 N 0.7637(15) 0.4413(3) 0.6272(5) 0.058(4) Uiso 1 1 d . . .
N2 N 0.4347(15) 0.5054(2) 0.6632(6) 0.061(4) Uiso 1 1 d . . .
N3 N 0.2057(16) 0.5040(3) 0.8232(6) 0.064(4) Uiso 1 1 d . . .
H3A H 0.1192 0.5314 0.8029 0.077 Uiso 1 1 calc . . .
H3B H 0.1752 0.4897 0.8852 0.077 Uiso 1 1 calc . . .
C1 C 0.711(2) 0.4172(3) 0.7250(9) 0.067(5) Uiso 1 1 d . . .
H1 H 0.8003 0.3867 0.7454 0.081 Uiso 1 1 calc . . .
C2 C 0.6117(19) 0.4846(3) 0.5924(7) 0.071(5) Uiso 1 1 d . . .
C3 C 0.387(2) 0.4836(3) 0.7585(8) 0.084(5) Uiso 1 1 d . . .
C4 C 0.879(2) 0.3939(3) 0.4565(6) 0.068(5) Uiso 1 1 d . . .
H4A H 0.9985 0.3978 0.3964 0.082 Uiso 1 1 calc . . .
H4B H 0.7078 0.4053 0.4339 0.082 Uiso 1 1 calc . . .
C5 C 0.532(2) 0.4377(3) 0.7900(8) 0.072(5) Uiso 1 1 d . . .
C6 C 1.180(2) 0.3410(4) 0.5777(7) 0.071(5) Uiso 1 1 d . . .
H6 H 1.3201 0.3411 0.5242 0.085 Uiso 1 1 calc . . .
C7 C 0.970(2) 0.4243(3) 0.5550(7) 0.071(5) Uiso 1 1 d . . .
H7 H 1.0623 0.4560 0.5299 0.085 Uiso 1 1 calc . . .
C8 C 1.255(2) 0.3051(3) 0.6683(8) 0.083(5) Uiso 1 1 d . . .
H8A H 1.2863 0.2697 0.6402 0.099 Uiso 1 1 calc . . .
H8B H 1.4138 0.3178 0.7011 0.099 Uiso 1 1 calc . . .
O4 O 0.0656(15) 0.6112(2) 0.7255(5) 0.065(3) Uiso 1 1 d . . .
O5 O 0.0172(15) 0.6935(2) 0.7746(6) 0.077(3) Uiso 1 1 d . . .
N4 N 0.5428(17) 0.6223(3) 0.6559(6) 0.066(4) Uiso 1 1 d . . .
H4C H 0.4433 0.5934 0.6666 0.079 Uiso 1 1 calc . . .
H4D H 0.6983 0.6164 0.6865 0.079 Uiso 1 1 calc . . .
C9 C 0.420(2) 0.6694(3) 0.7057(9) 0.078(5) Uiso 1 1 d . . .
H9 H 0.5132 0.6796 0.7716 0.094 Uiso 1 1 calc . . .
C10 C 0.444(2) 0.7125(4) 0.6209(8) 0.077(5) Uiso 1 1 d . . .
H10A H 0.2993 0.7370 0.6255 0.092 Uiso 1 1 calc . . .
H10B H 0.6036 0.7321 0.6300 0.092 Uiso 1 1 calc . . .
C11 C 0.442(2) 0.6842(3) 0.5166(7) 0.067(5) Uiso 1 1 d . . .
H11A H 0.5339 0.7043 0.4619 0.080 Uiso 1 1 calc . . .
H11B H 0.2653 0.6785 0.4920 0.080 Uiso 1 1 calc . . .
C12 C 0.574(2) 0.6323(4) 0.5377(6) 0.076(5) Uiso 1 1 d . . .
H12A H 0.4944 0.6041 0.4958 0.091 Uiso 1 1 calc . . .
H12B H 0.7560 0.6344 0.5186 0.091 Uiso 1 1 calc . . .
C13 C 0.143(2) 0.6574(3) 0.7321(9) 0.087(5) 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
S1 C4 1.800(8) . ?
S1 C6 1.833(11) . ?
F1 C5 1.353(11) . ?
O1 C2 1.227(11) . ?
O2 C6 1.407(11) . ?
O2 C7 1.420(12) . ?
O3 C8 1.411(13) . ?
O3 H3 0.8200 . ?
N1 C1 1.378(12) . ?
N1 C2 1.411(11) . ?
N1 C7 1.455(12) . ?
N2 C3 1.321(12) . ?
N2 C2 1.369(12) . ?
N3 C3 1.335(13) . ?
N3 H3A 0.8598 . ?
N3 H3B 0.8602 . ?
C1 C5 1.329(15) . ?
C1 H1 0.9301 . ?
C3 C5 1.431(13) . ?
C4 C7 1.512(12) . ?
C4 H4A 0.9699 . ?
C4 H4B 0.9699 . ?
C6 C8 1.489(13) . ?
C6 H6 0.9798 . ?
C7 H7 0.9801 . ?
C8 H8A 0.9699 . ?
C8 H8B 0.9702 . ?
O4 C13 1.233(11) . ?
O5 C13 1.234(12) . ?
N4 C9 1.480(12) . ?
N4 C12 1.489(10) . ?
N4 H4C 0.8998 . ?
N4 H4D 0.8999 . ?
C9 C13 1.498(17) . ?
C9 C10 1.514(13) . ?
C9 H9 0.9798 . ?
C10 C11 1.471(13) . ?
C10 H10A 0.9701 . ?
C10 H10B 0.9700 . ?
C11 C12 1.499(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9701 . ?
C12 H12A 0.9701 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C6 88.5(5) . . ?
C6 O2 C7 114.5(7) . . ?
C8 O3 H3 109.5 . . ?
C1 N1 C2 119.8(8) . . ?
C1 N1 C7 123.5(8) . . ?
C2 N1 C7 116.7(7) . . ?
C3 N2 C2 122.2(7) . . ?
C3 N3 H3A 120.0 . . ?
C3 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C5 C1 N1 119.7(8) . . ?
C5 C1 H1 120.2 . . ?
N1 C1 H1 120.2 . . ?
O1 C2 N2 121.9(8) . . ?
O1 C2 N1 119.8(8) . . ?
N2 C2 N1 118.2(7) . . ?
N2 C3 N3 120.2(8) . . ?
N2 C3 C5 118.8(9) . . ?
N3 C3 C5 121.0(9) . . ?
C7 C4 S1 101.5(5) . . ?
C7 C4 H4A 111.5 . . ?
S1 C4 H4A 111.4 . . ?
C7 C4 H4B 111.5 . . ?
S1 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
C1 C5 F1 121.8(8) . . ?
C1 C5 C3 120.9(9) . . ?
F1 C5 C3 116.9(9) . . ?
O2 C6 C8 110.1(7) . . ?
O2 C6 S1 103.7(7) . . ?
C8 C6 S1 117.5(7) . . ?
O2 C6 H6 108.4 . . ?
C8 C6 H6 108.4 . . ?
S1 C6 H6 108.4 . . ?
O2 C7 N1 107.8(7) . . ?
O2 C7 C4 110.3(7) . . ?
N1 C7 C4 114.4(9) . . ?
O2 C7 H7 108.0 . . ?
N1 C7 H7 108.0 . . ?
C4 C7 H7 108.0 . . ?
O3 C8 C6 110.8(8) . . ?
O3 C8 H8A 109.5 . . ?
C6 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 N4 C12 108.5(7) . . ?
C9 N4 H4C 110.0 . . ?
C12 N4 H4C 110.0 . . ?
C9 N4 H4D 110.0 . . ?
C12 N4 H4D 110.0 . . ?
H4C N4 H4D 108.4 . . ?
N4 C9 C13 109.8(8) . . ?
N4 C9 C10 104.6(8) . . ?
C13 C9 C10 111.9(9) . . ?
N4 C9 H9 110.1 . . ?
C13 C9 H9 110.1 . . ?
C10 C9 H9 110.1 . . ?
C11 C10 C9 104.9(7) . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10B 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C12 105.5(7) . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
N4 C12 C11 105.6(7) . . ?
N4 C12 H12A 110.6 . . ?
C11 C12 H12A 110.6 . . ?
N4 C12 H12B 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
O4 C13 O5 123.7(11) . . ?
O4 C13 C9 119.0(9) . . ?
O5 C13 C9 116.4(8) . . ?

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

O3 H3 O5 0.83 2.03 2.799(7) 155 4_646
N3 H3A O4 0.86 2.24 3.045(9) 155 .
N3 H3B F1 0.86 2.42 2.736(9) 102 .
N3 H3B O1 0.86 2.21 2.873(10) 133 2_565
N4 H4C O4 0.90 2.13 2.625(11) 114 .
N4 H4C N2 0.90 2.22 2.999(9) 145 .
N4 H4D O4 0.90 1.96 2.847(12) 168 1_655

_refine_diff_density_max         0.42
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.22
_exptl_crystal_colour            Colorless
