# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_cit1001
_database_code_depnum_ccdc_archive 'CCDC 2279352'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H7 N O, C7 H7 N O2'
_chemical_formula_sum            'C10 H14 N2 O3'
_chemical_formula_weight         210.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H6 N1 O2'
_chemical_oxdiff_usercomment     'PABA - DMF'
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'
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                   9.1603(7)
_cell_length_b                   11.1181(8)
_cell_length_c                   11.9004(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.772(9)
_cell_angle_gamma                90
_cell_volume                     1133.22(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9130
_cell_measurement_theta_min      2.9860
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0170
_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       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11747
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.433
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    5.00    --  -17.15 -99.00  90.00   45
  2  ω    -50.00  40.00   1.00    5.00    --   18.87 -57.00 -60.00   90
  3  ω    -50.00  40.00   1.00    5.00    --   18.87 -57.00-180.00   90
  4  ω    -51.00  49.00   1.00    5.00    --   18.87 -77.00  60.00  100
  5  ω    -87.00  13.00   1.00    5.00    --  -17.15 -77.00 -60.00  100
  6  ω    -20.00  10.00   1.00    5.00    --  -17.15 -99.00 150.00   30
  7  ω     -3.00  88.00   1.00    5.00    --   18.87  57.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344677000
_diffrn_orient_matrix_UB_12      0.0391649000
_diffrn_orient_matrix_UB_13      -0.0305712000
_diffrn_orient_matrix_UB_21      -0.0201627000
_diffrn_orient_matrix_UB_22      0.0501505000
_diffrn_orient_matrix_UB_23      0.0283550000
_diffrn_orient_matrix_UB_31      0.0725418000
_diffrn_orient_matrix_UB_32      -0.0047044000
_diffrn_orient_matrix_UB_33      0.0482187000
_diffrn_oxdiff_ac4_digest_frames 
;
01fd32562cb657f2b4fc8b0e6c31a7d0400002732d2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1676
_reflns_number_total             2308
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.039
_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)+(0.0717P)²+0.2611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C2(H2A), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.2030(2) 0.49049(15) 0.83961(14) 0.0674(5) Uani 1 1 d . . . . .
O3 O 0.2768(2) 0.46884(16) 0.67911(14) 0.0883(5) Uani 1 1 d . . . . .
C8 C 0.2828(3) 0.4395(2) 0.7801(2) 0.0773(6) Uani 1 1 d . . . . .
H8 H 0.348880 0.376358 0.817214 0.093 Uiso 1 1 calc R U . . .
C9 C 0.2128(5) 0.4499(3) 0.9575(3) 0.1296(13) Uani 1 1 d . . . . .
H9A H 0.112108 0.422100 0.954260 0.194 Uiso 1 1 calc R U . . .
H9B H 0.245814 0.515246 1.013570 0.194 Uiso 1 1 calc R U . . .
H9C H 0.286828 0.385303 0.983006 0.194 Uiso 1 1 calc R U . . .
C10 C 0.0925(3) 0.5849(3) 0.7847(2) 0.0963(8) Uani 1 1 d . . . . .
H10A H 0.074143 0.587829 0.700175 0.144 Uiso 1 1 calc R U . . .
H10B H 0.133793 0.660604 0.820803 0.144 Uiso 1 1 calc R U . . .
H10C H -0.003957 0.568882 0.796671 0.144 Uiso 1 1 calc R U . . .
O1 O 0.15364(18) 0.24941(14) 0.46285(14) 0.0785(5) Uani 1 1 d . . . . .
N1 N 0.4009(3) 0.1493(2) 0.03435(19) 0.0795(6) Uani 1 1 d . . . . .
C1 C 0.3707(2) 0.18289(17) 0.13358(16) 0.0576(5) Uani 1 1 d . . . . .
O2 O 0.35887(18) 0.37183(14) 0.51094(13) 0.0733(5) Uani 1 1 d . . . . .
C2 C 0.4627(2) 0.26811(18) 0.21386(17) 0.0622(5) Uani 1 1 d . . . . .
H2A H 0.547853 0.301491 0.199914 0.075 Uiso 1 1 calc R U . . .
C3 C 0.4303(2) 0.30354(18) 0.31269(16) 0.0591(5) Uani 1 1 d . . . . .
H3 H 0.493249 0.360644 0.364615 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3038(2) 0.25497(16) 0.33633(15) 0.0526(4) Uani 1 1 d . . . . .
C5 C 0.2122(2) 0.17051(18) 0.25664(17) 0.0605(5) Uani 1 1 d . . . . .
H5 H 0.127160 0.137310 0.270831 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2437(2) 0.13480(19) 0.15764(17) 0.0627(5) Uani 1 1 d . . . . .
H6 H 0.180115 0.077950 0.105779 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2640(2) 0.29041(17) 0.44084(16) 0.0571(5) Uani 1 1 d . . . . .
H1A H 0.474(3) 0.176(2) 0.020(2) 0.087(8) Uiso 1 1 d . . . . .
H1B H 0.347(3) 0.097(2) -0.018(2) 0.085(8) Uiso 1 1 d . . . . .
H2 H 0.330(3) 0.392(3) 0.572(3) 0.112(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
N2 C8 1.313(3) . ?
N2 C9 1.447(3) . ?
N2 C10 1.443(3) . ?
O3 C8 1.227(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1 C7 1.219(2) . ?
N1 C1 1.357(3) . ?
N1 H1A 0.80(3) . ?
N1 H1B 0.87(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.399(3) . ?
O2 C7 1.325(2) . ?
O2 H2 0.89(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(2) . ?
C4 C5 1.386(3) . ?
C4 C7 1.469(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(3) . ?
C6 H6 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
C8 N2 C9 122.3(2) . . ?
C8 N2 C10 120.32(19) . . ?
C10 N2 C9 117.2(2) . . ?
N2 C8 H8 117.5 . . ?
O3 C8 N2 125.0(2) . . ?
O3 C8 H8 117.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 H1A 121.4(18) . . ?
C1 N1 H1B 124.7(16) . . ?
H1A N1 H1B 114(2) . . ?
N1 C1 C2 121.49(19) . . ?
N1 C1 C6 120.9(2) . . ?
C2 C1 C6 117.61(17) . . ?
C7 O2 H2 111.8(19) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 C1 121.36(17) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.73(18) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 122.74(17) . . ?
C5 C4 C3 117.99(16) . . ?
C5 C4 C7 119.27(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.62(17) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.69(18) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 O2 121.93(17) . . ?
O1 C7 C4 123.76(18) . . ?
O2 C7 C4 114.31(16) . . ?

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
C9 N2 C8 O3 178.6(3) . . . . ?
C10 N2 C8 O3 3.2(4) . . . . ?
N1 C1 C2 C3 178.7(2) . . . . ?
N1 C1 C6 C5 -178.85(19) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C7 -179.76(17) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C7 O1 179.70(18) . . . . ?
C3 C4 C7 O2 -0.4(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C5 C4 C7 O1 0.2(3) . . . . ?
C5 C4 C7 O2 -179.85(16) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C4 C5 C6 179.68(17) . . . . ?

_olex2_submission_original_sample_id 'PABA + DMF'
_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 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.651
