# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_3129
_database_code_depnum_ccdc_archive 'CCDC 2287475'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Feng'
;Hunan University
China
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2023-07-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
methyl-1-(cyanomethyl)-3-phenylcyclobut-2-ene-1-carboxylate
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C100 H100 N2 O2'
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'
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           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                   10.84837(19)
_cell_length_b                   8.49086(12)
_cell_length_c                   14.3960(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.998(2)
_cell_angle_gamma                90
_cell_volume                     1229.50(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5358
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      71.5750
_cell_measurement_theta_min      4.3890
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.403
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  43.00   1.00    2.00    --   34.73 -57.00  90.00   60
  2  ω     31.00  73.00   1.00    2.00    --   34.73-125.00   0.00   42
  3  ω     36.00  85.00   1.00    8.00    --  105.25 -94.00 -30.00   49
  4  ω     88.00 174.00   1.00    8.00    --  105.25  45.00  90.00   86
  5  ω    116.00 162.00   1.00    8.00    --  105.25  77.00 120.00   46
  6  ω    107.00 140.00   1.00    8.00    --  105.25  96.00  19.00   33
  7  ω     83.00 111.00   1.00    8.00    --  105.25  77.00 120.00   28
  8  ω     44.00 102.00   1.00    2.00    --   34.73  77.00  60.00   58
  9  ω    106.00 161.00   1.00    8.00    --  105.25 111.00-180.00   55
 10  ω    -31.00  14.00   1.00    2.00    --   34.73 -77.00 -30.00   45
 11  ω     65.00  93.00   1.00    2.00    --   34.73  57.00 -90.00   28
 12  ω     20.00  56.00   1.00    2.00    --   34.73  57.00-150.00   36
 13  ω    -37.00  63.00   1.00    2.00    --   34.73 -19.00 150.00  100
 14  ω      3.00  73.00   1.00    2.00    --   34.73 -99.00  30.00   70
 15  ω     49.00  88.00   1.00    2.00    --   34.73-125.00-180.00   39
 16  ω     17.00  55.00   1.00    2.00    --   34.73 -99.00 -90.00   38
 17  ω     89.00 114.00   1.00    8.00    --  105.25 -45.00-120.00   25
 18  ω    113.00 152.00   1.00    8.00    --  105.25 111.00  30.00   39
 19  ω     45.00 127.00   1.00    8.00    --  105.25 -30.00  60.00   82
 20  ω     36.00 108.00   1.00    8.00    --  105.25-111.00-120.00   72
 21  ω     45.00  77.00   1.00    8.00    --  105.25 -45.00-120.00   32
 22  ω    112.00 138.00   1.00    8.00    --  105.25 111.00 -60.00   26
 23  ω     43.00 108.00   1.00    8.00    --  105.25 -94.00  30.00   65
 24  ω     76.00 121.00   1.00    8.00    --  105.25 -61.00   0.00   45
 25  ω     61.00 102.00   1.00    8.00    --  105.25 -94.00 120.00   41
 26  ω     47.00 108.00   1.00    8.00    --  105.25 -94.00 -90.00   61
 27  ω    100.00 143.00   1.00    8.00    --  105.25 111.00 150.00   43
 28  ω     44.00  70.00   1.00    8.00    --  105.25 -94.00-180.00   26
 29  ω     84.00 139.00   1.00    8.00    --  105.25  77.00-150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1044367000
_diffrn_orient_matrix_UB_12      -0.0874469000
_diffrn_orient_matrix_UB_13      -0.0884212000
_diffrn_orient_matrix_UB_21      0.0291276000
_diffrn_orient_matrix_UB_22      -0.1531693000
_diffrn_orient_matrix_UB_23      0.0619404000
_diffrn_orient_matrix_UB_31      -0.1081371000
_diffrn_orient_matrix_UB_32      0.0431322000
_diffrn_orient_matrix_UB_33      0.0407444000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2012
_reflns_number_total             2160
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      3.501
_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)+(0.0796P)²+0.3909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C8
 2.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C10(H10)
3.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_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
O1 O 0.21046(12) 0.40335(15) -0.00731(9) 0.0518(4) Uani 1 1 d . . . . .
N1 N 0.43062(19) 0.5124(2) 0.33448(13) 0.0688(5) Uani 1 1 d . . . . .
C1 C 0.5288(2) 0.8981(3) -0.16045(18) 0.0743(7) Uani 1 1 d . . . . .
H1 H 0.615015 0.888869 -0.158731 0.089 Uiso 1 1 calc R U . . .
O2 O 0.12838(15) 0.43314(17) 0.11260(11) 0.0630(4) Uani 1 1 d . . . . .
C2 C 0.4371(3) 0.9844(3) -0.23465(17) 0.0769(7) Uani 1 1 d . . . . .
H2 H 0.460565 1.032816 -0.283581 0.092 Uiso 1 1 calc R U . . .
C3 C 0.3106(3) 0.9991(3) -0.23649(18) 0.0762(7) Uani 1 1 d . . . . .
H3 H 0.248310 1.058123 -0.286733 0.091 Uiso 1 1 calc R U . . .
C4 C 0.2745(2) 0.9268(2) -0.16407(15) 0.0585(5) Uani 1 1 d . . . . .
H4 H 0.188436 0.938231 -0.165644 0.070 Uiso 1 1 calc R U . . .
C5 C 0.36609(16) 0.83757(19) -0.08949(12) 0.0425(4) Uani 1 1 d . . . . .
C6 C 0.49423(19) 0.8244(3) -0.08800(15) 0.0571(5) Uani 1 1 d . . . . .
H6 H 0.557266 0.765718 -0.038018 0.068 Uiso 1 1 calc R U . . .
C7 C 0.32905(16) 0.75678(18) -0.01501(12) 0.0395(4) Uani 1 1 d D . . . .
C8 C 0.20469(17) 0.7566(2) 0.00294(12) 0.0438(4) Uani 1 1 d D . . . .
H8A H 0.129152 0.715550 -0.052555 0.053 Uiso 1 1 calc R U . . .
H8B H 0.183699 0.857184 0.025411 0.053 Uiso 1 1 calc R U . . .
C9 C 0.26825(15) 0.63587(19) 0.08891(11) 0.0376(4) Uani 1 1 d . . . . .
C10 C 0.39325(16) 0.6488(2) 0.06262(13) 0.0435(4) Uani 1 1 d . . . . .
H10 H 0.477396 0.603480 0.087860 0.052 Uiso 1 1 calc R U . . .
C11 C 0.28290(17) 0.6972(2) 0.19257(12) 0.0448(4) Uani 1 1 d . . . . .
H11A H 0.321963 0.801569 0.202065 0.054 Uiso 1 1 calc R U . . .
H11B H 0.195537 0.705821 0.195973 0.054 Uiso 1 1 calc R U . . .
C12 C 0.36576(18) 0.5943(2) 0.27299(13) 0.0468(4) Uani 1 1 d . . . . .
C13 C 0.19556(15) 0.48006(19) 0.06818(11) 0.0393(4) Uani 1 1 d . . . . .
C14 C 0.1339(2) 0.2602(2) -0.04028(16) 0.0617(5) Uani 1 1 d . . . . .
H14A H 0.155612 0.212366 -0.092653 0.093 Uiso 1 1 calc R U . . .
H14B H 0.040794 0.284814 -0.065091 0.093 Uiso 1 1 calc R U . . .
H14C H 0.154614 0.188464 0.015043 0.093 Uiso 1 1 calc R U . . .


_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 C13 1.328(2) . ?
O1 C14 1.448(2) . ?
N1 C12 1.138(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(4) . ?
C1 C6 1.383(3) . ?
O2 C13 1.203(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 C6 1.387(2) . ?
C5 C7 1.451(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.466(2) . ?
C7 C10 1.411(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.555(2) . ?
C9 C10 1.542(2) . ?
C9 C11 1.531(2) . ?
C9 C13 1.512(2) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.460(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C13 O1 C14 116.71(14) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.5(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.74(17) . . ?
C4 C5 C7 120.99(16) . . ?
C6 C5 C7 120.26(16) . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C7 C8 131.22(15) . . ?
C10 C7 C5 134.54(15) . . ?
C10 C7 C8 94.22(13) . . ?
C7 C8 H8A 113.9 . . ?
C7 C8 H8B 113.9 . . ?
C7 C8 C9 88.74(12) . . ?
H8A C8 H8B 111.1 . . ?
C9 C8 H8A 113.9 . . ?
C9 C8 H8B 113.9 . . ?
C10 C9 C8 85.77(12) . . ?
C11 C9 C8 113.87(13) . . ?
C11 C9 C10 115.79(13) . . ?
C13 C9 C8 112.13(12) . . ?
C13 C9 C10 117.09(13) . . ?
C13 C9 C11 110.23(13) . . ?
C7 C10 C9 91.27(12) . . ?
C7 C10 H10 134.4 . . ?
C9 C10 H10 134.4 . . ?
C9 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C9 112.19(14) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N1 C12 C11 178.8(2) . . ?
O1 C13 C9 112.12(13) . . ?
O2 C13 O1 123.79(16) . . ?
O2 C13 C9 124.05(15) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C7 -178.0(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C7 C8 -4.2(3) . . . . ?
C4 C5 C7 C10 173.29(19) . . . . ?
C5 C7 C8 C9 177.64(17) . . . . ?
C5 C7 C10 C9 -177.53(18) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C5 C7 C8 176.83(17) . . . . ?
C6 C5 C7 C10 -5.6(3) . . . . ?
C7 C5 C6 C1 178.35(19) . . . . ?
C7 C8 C9 C10 0.54(12) . . . . ?
C7 C8 C9 C11 116.93(14) . . . . ?
C7 C8 C9 C13 -117.04(13) . . . . ?
C8 C7 C10 C9 0.60(13) . . . . ?
C8 C9 C10 C7 -0.56(12) . . . . ?
C8 C9 C11 C12 -168.69(14) . . . . ?
C8 C9 C13 O1 68.38(17) . . . . ?
C8 C9 C13 O2 -109.32(19) . . . . ?
C10 C7 C8 C9 -0.59(13) . . . . ?
C10 C9 C11 C12 -71.54(19) . . . . ?
C10 C9 C13 O1 -28.44(19) . . . . ?
C10 C9 C13 O2 153.86(17) . . . . ?
C11 C9 C10 C7 -115.08(15) . . . . ?
C11 C9 C13 O1 -163.63(13) . . . . ?
C11 C9 C13 O2 18.7(2) . . . . ?
C13 C9 C10 C7 112.18(14) . . . . ?
C13 C9 C11 C12 64.29(18) . . . . ?
C14 O1 C13 O2 3.8(3) . . . . ?
C14 O1 C13 C9 -173.87(14) . . . . ?

_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 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.530
