# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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_s1150_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213069'
loop_
_audit_author_name
_audit_author_address
'Diaz-Rodriguez R.M.'
;University of Ottawa
Canada
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rdiaz030@uottawa.ca
_chemical_name_common            ?
_chemical_name_systematic        '(2E)-2-cyano-3-cyclopropyl-2-propenoic acid'
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.290(4)
_cell_length_b                   12.586(6)
_cell_length_c                   7.891(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.778(13)
_cell_angle_gamma                90
_cell_volume                     708.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.456
_cell_measurement_theta_min      3.094
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1592 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8609.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.1900
1.00 -1.00 -1.00 0.1770
-1.00 1.00 1.00 0.0920
1.00 0.00 -1.00 0.1340
-1.00 0.00 1.00 0.0670
-1.00 -1.00 1.00 0.0740
1.00 1.00 -1.00 0.1780
0.00 1.00 1.00 0.1240
0.00 -1.00 -1.00 0.1860
0.00 0.00 1.00 0.0610
0.00 0.00 -1.00 0.1600
0.00 -1.00 1.00 0.1370
0.00 1.00 -1.00 0.1840
-1.00 -1.00 -1.00 0.2090
-1.00 1.00 -1.00 0.2250
0.00 -1.00 0.00 0.2660
0.00 1.00 0.00 0.2410
1.00 -1.00 1.00 0.2180

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Crystallized directly from reaction mixture (toluene)'
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.447
_exptl_crystal_size_min          0.268
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5635
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.669
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                873
_reflns_number_total             1342
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1342
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.056
_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)+(0.0537P)²+0.1996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H1-O1
 0.86 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
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 0.0632(2) 0.63384(12) 0.0114(2) 0.0645(5) Uani 1 1 d D . . . .
O2 O 0.2319(2) 0.48740(11) 0.0898(2) 0.0679(5) Uani 1 1 d . . . . .
C1 C 0.2130(3) 0.58717(15) 0.0839(3) 0.0494(5) Uani 1 1 d . . . . .
C2 C 0.3707(3) 0.65389(15) 0.1685(3) 0.0486(5) Uani 1 1 d . . . . .
C4 C 0.5304(3) 0.61201(15) 0.2565(3) 0.0522(5) Uani 1 1 d . . . . .
H4 H 0.539129 0.538287 0.257037 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6906(3) 0.66902(17) 0.3506(3) 0.0582(6) Uani 1 1 d . . . . .
H5 H 0.684983 0.746769 0.345063 0.070 Uiso 1 1 calc R U . . .
C3 C 0.3432(3) 0.76641(17) 0.1599(3) 0.0631(6) Uani 1 1 d . . . . .
C7 C 0.8817(3) 0.61856(19) 0.3673(3) 0.0672(7) Uani 1 1 d . . . . .
H7A H 0.888680 0.550756 0.310562 0.081 Uiso 1 1 calc R U . . .
H7B H 0.987538 0.665314 0.367725 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7960(3) 0.6203(2) 0.5178(3) 0.0731(7) Uani 1 1 d . . . . .
H6A H 0.848592 0.668183 0.611486 0.088 Uiso 1 1 calc R U . . .
H6B H 0.749724 0.553615 0.554317 0.088 Uiso 1 1 calc R U . . .
N1 N 0.3238(3) 0.85626(15) 0.1575(4) 0.1038(10) Uani 1 1 d . . . . .
H1 H -0.034(4) 0.593(3) -0.022(5) 0.168(16) Uiso 1 1 d D . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0448(8) 0.0494(9) 0.0872(11) 0.0038(8) -0.0150(7) -0.0003(7)
O2 0.0588(10) 0.0391(8) 0.0923(12) 0.0011(7) -0.0165(8) -0.0053(7)
C1 0.0472(11) 0.0384(10) 0.0569(12) 0.0026(9) -0.0031(9) -0.0015(9)
C2 0.0438(11) 0.0350(10) 0.0611(12) 0.0019(8) -0.0030(9) -0.0032(8)
C4 0.0461(12) 0.0374(10) 0.0665(13) 0.0022(9) -0.0039(9) -0.0025(9)
C5 0.0477(12) 0.0413(11) 0.0760(15) 0.0011(10) -0.0102(10) -0.0041(9)
C3 0.0431(12) 0.0433(13) 0.0913(17) 0.0011(11) -0.0134(11) -0.0028(10)
C7 0.0444(12) 0.0657(15) 0.0831(17) -0.0077(12) -0.0069(11) -0.0022(11)
C6 0.0636(15) 0.0787(17) 0.0660(15) 0.0018(12) -0.0128(12) -0.0055(13)
N1 0.0692(14) 0.0414(11) 0.177(3) -0.0031(13) -0.0318(15) 0.0000(10)

_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 C1 1.269(2) . ?
O1 H1 0.875(10) . ?
O2 C1 1.263(2) . ?
C1 C2 1.469(3) . ?
C2 C4 1.336(3) . ?
C2 C3 1.430(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.441(3) . ?
C5 H5 0.9800 . ?
C5 C7 1.512(3) . ?
C5 C6 1.514(3) . ?
C3 N1 1.139(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.450(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 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
C1 O1 H1 115(3) . . ?
O1 C1 C2 117.51(18) . . ?
O2 C1 O1 123.66(18) . . ?
O2 C1 C2 118.82(18) . . ?
C4 C2 C1 121.91(18) . . ?
C4 C2 C3 120.94(18) . . ?
C3 C2 C1 117.08(17) . . ?
C2 C4 H4 116.6 . . ?
C2 C4 C5 126.86(19) . . ?
C5 C4 H4 116.6 . . ?
C4 C5 H5 116.9 . . ?
C4 C5 C7 118.09(19) . . ?
C4 C5 C6 117.47(19) . . ?
C7 C5 H5 116.9 . . ?
C7 C5 C6 57.27(15) . . ?
C6 C5 H5 116.9 . . ?
N1 C3 C2 178.2(3) . . ?
C5 C7 H7A 117.6 . . ?
C5 C7 H7B 117.6 . . ?
H7A C7 H7B 114.7 . . ?
C6 C7 C5 61.43(15) . . ?
C6 C7 H7A 117.6 . . ?
C6 C7 H7B 117.6 . . ?
C5 C6 H6A 117.6 . . ?
C5 C6 H6B 117.6 . . ?
C7 C6 C5 61.30(16) . . ?
C7 C6 H6A 117.6 . . ?
C7 C6 H6B 117.6 . . ?
H6A C6 H6B 114.7 . . ?

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
O1 C1 C2 C4 176.2(2) . . . . ?
O1 C1 C2 C3 -0.9(3) . . . . ?
O2 C1 C2 C4 -2.5(3) . . . . ?
O2 C1 C2 C3 -179.5(2) . . . . ?
C1 C2 C4 C5 -177.1(2) . . . . ?
C2 C4 C5 C7 -151.1(2) . . . . ?
C2 C4 C5 C6 143.3(2) . . . . ?
C4 C5 C7 C6 -106.2(2) . . . . ?
C4 C5 C6 C7 107.3(2) . . . . ?
C3 C2 C4 C5 -0.1(4) . . . . ?

_shelx_res_file                  
;
TITL S1150_0m_a.res in P2(1)/c
    s1150_0m_a.res
    created by SHELXL-2018/3 at 17:19:50 on 16-May-2022
REM Old TITL S1150_0m in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.244, Rweak 0.005, Alpha 0.023, Orientation as input
REM Formula found by SHELXT: C7 N O2
CELL 0.71073 7.2896 12.586 7.891 90 101.778 90
ZERR 4 0.0037 0.0064 0.0042 0 0.013 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 28 28 4 8
DFIX 0.86 0.01 H1 O1

L.S. 99
PLAN  15
SIZE 0.268 0.447 0.461
TEMP 20
CONF
BOND $H
LIST 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\S1150_0m_a.hkl">
REM </olex2.extras>

WGHT    0.053700    0.199600
FVAR       0.67314
O1    4    0.063190    0.633842    0.011386    11.00000    0.04479    0.04943 =
         0.08724    0.00380   -0.01496   -0.00028
O2    4    0.231901    0.487396    0.089826    11.00000    0.05882    0.03911 =
         0.09228    0.00107   -0.01650   -0.00526
C1    1    0.213006    0.587173    0.083908    11.00000    0.04716    0.03842 =
         0.05685    0.00256   -0.00310   -0.00153
C2    1    0.370743    0.653891    0.168469    11.00000    0.04377    0.03498 =
         0.06115    0.00186   -0.00299   -0.00316
C4    1    0.530437    0.612011    0.256490    11.00000    0.04613    0.03745 =
         0.06648    0.00221   -0.00391   -0.00250
AFIX  43
H4    2    0.539129    0.538287    0.257037    11.00000   -1.20000
AFIX   0
C5    1    0.690563    0.669021    0.350630    11.00000    0.04769    0.04126 =
         0.07602    0.00115   -0.01015   -0.00408
AFIX  13
H5    2    0.684983    0.746769    0.345063    11.00000   -1.20000
AFIX   0
C3    1    0.343212    0.766406    0.159935    11.00000    0.04309    0.04331 =
         0.09134    0.00111   -0.01343   -0.00279
C7    1    0.881675    0.618557    0.367345    11.00000    0.04443    0.06571 =
         0.08307   -0.00768   -0.00692   -0.00219
AFIX  23
H7A   2    0.888680    0.550756    0.310562    11.00000   -1.20000
H7B   2    0.987538    0.665314    0.367725    11.00000   -1.20000
AFIX   0
C6    1    0.795963    0.620310    0.517806    11.00000    0.06358    0.07866 =
         0.06597    0.00181   -0.01278   -0.00551
AFIX  23
H6A   2    0.848592    0.668183    0.611486    11.00000   -1.20000
H6B   2    0.749724    0.553615    0.554317    11.00000   -1.20000
AFIX   0
N1    3    0.323833    0.856256    0.157548    11.00000    0.06917    0.04135 =
         0.17653   -0.00308   -0.03178   -0.00001
H1    2   -0.034044    0.592558   -0.021696    11.00000    0.16821
HKLF 4




REM  S1150_0m_a.res in P2(1)/c
REM wR2 = 0.1316, GooF = S = 1.056, Restrained GooF = 1.056 for all data
REM R1 = 0.0427 for 873 Fo > 4sig(Fo) and 0.0753 for all 1342 data
REM 95 parameters refined using 1 restraints

END

WGHT      0.0537      0.1996

REM Highest difference peak  0.152,  deepest hole -0.187,  1-sigma level  0.039
Q1    1   0.3024  0.5005 -0.0622  11.00000  0.05    0.15
Q2    1   0.1543  0.4395  0.0737  11.00000  0.05    0.14
Q3    1   0.1680  0.4985  0.2216  11.00000  0.05    0.12
Q4    1   0.2762  0.5172 -0.0033  11.00000  0.05    0.12
Q5    1   0.9921  0.6235  0.2257  11.00000  0.05    0.12
Q6    1   0.9630  0.6533  0.1813  11.00000  0.05    0.11
Q7    1   0.2579  0.7970  0.3233  11.00000  0.05    0.11
Q8    1   0.0650  0.7228  0.0029  11.00000  0.05    0.11
Q9    1   0.2501  0.8164  0.1956  11.00000  0.05    0.11
Q10   1   0.3294  0.8265  0.0491  11.00000  0.05    0.11
Q11   1   0.1589  0.6805 -0.1099  11.00000  0.05    0.10
Q12   1   0.7372  0.6210  0.6760  11.00000  0.05    0.10
Q13   1   0.7824  0.6393  0.3505  11.00000  0.05    0.10
Q14   1   0.1444  0.6210 -0.1457  11.00000  0.05    0.10
Q15   1   0.7576  0.7134  0.6180  11.00000  0.05    0.10
;
_shelx_res_checksum              83210
_olex2_date_sample_submission    2022-05-14
_olex2_exptl_crystal_mounting_method 
'Mounted on a 200uM MicroLoop with Parabar 10312 oil'
_olex2_submission_original_sample_id S1150_LM-1-73
_olex2_submission_special_instructions 'No special instructions were received'
