# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_pas5
_audit_block_doi                 10.5517/ccdc.csd.cc23ntwh
_database_code_depnum_ccdc_archive 'CCDC 1956437'
loop_
_audit_author_name
_audit_author_address
'Alexander Koronatov'
;SPbSU
Russia
;
_audit_update_record             
;
2019-09-28 deposited with the CCDC.	2019-11-14 downloaded from the CCDC.
;
_audit_creation_date             2019-08-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        '3-phenyl-2H-azirine-2-carboxylic acid'
_chemical_formula_moiety         'C9 H7 N O2'
_chemical_formula_sum            'C9 H7 N O2'
_chemical_formula_weight         161.16
_chemical_melting_point          378-380
_chemical_oxdiff_formula         'C9 N O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.0481(9)
_cell_length_b                   9.7876(9)
_cell_length_c                   10.8529(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.525(13)
_cell_angle_gamma                90
_cell_volume                     795.28(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6800
_cell_measurement_theta_min      2.8980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4098
_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         28.496
_diffrn_reflns_theta_min         2.721
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   12.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -19.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   15.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -98.00  -35.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00    9.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   92.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00  -27.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   57.0000  -90.0000 16
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0461087000
_diffrn_orient_matrix_UB_12      -0.0623921000
_diffrn_orient_matrix_UB_13      -0.0029141000
_diffrn_orient_matrix_UB_21      0.0713970000
_diffrn_orient_matrix_UB_22      -0.0362108000
_diffrn_orient_matrix_UB_23      -0.0084690000
_diffrn_orient_matrix_UB_31      0.0419419000
_diffrn_orient_matrix_UB_32      -0.0068750000
_diffrn_orient_matrix_UB_33      0.0697010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1652
_reflns_number_total             2004
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.333
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.042
_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)+(0.0379P)²+0.2179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C6(H6), C8(H8), C7(H7)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.61005(12) 0.21640(9) 0.38659(9) 0.0188(2) Uani 1 1 d . . . . .
O2 O 0.41149(13) 0.32431(10) 0.45465(9) 0.0214(2) Uani 1 1 d . . . . .
H2 H 0.4369 0.2631 0.5101 0.032 Uiso 1 1 calc GR . . . .
N1 N 0.48864(14) 0.37486(12) 0.14548(10) 0.0176(2) Uani 1 1 d . . . . .
C3 C 0.50502(16) 0.30836(13) 0.37668(12) 0.0153(3) Uani 1 1 d . . . . .
C4 C 0.76626(16) 0.52680(13) 0.24141(12) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.60147(16) 0.45497(13) 0.22231(12) 0.0156(3) Uani 1 1 d . . . . .
C1 C 0.46418(16) 0.41776(13) 0.27474(12) 0.0160(3) Uani 1 1 d . . . . .
H1 H 0.3715 0.4848 0.2697 0.019 Uiso 1 1 calc R . . . .
C9 C 0.83830(17) 0.52227(13) 0.14178(12) 0.0179(3) Uani 1 1 d . . . . .
H9 H 0.7801 0.4748 0.0635 0.021 Uiso 1 1 calc R . . . .
C5 C 0.85236(17) 0.59821(13) 0.35879(12) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.8032 0.6015 0.4240 0.023 Uiso 1 1 calc R . . . .
C6 C 1.01254(18) 0.66450(14) 0.37730(14) 0.0237(3) Uani 1 1 d . . . . .
H6 H 1.0715 0.7116 0.4557 0.028 Uiso 1 1 calc R . . . .
C8 C 0.99768(17) 0.58963(14) 0.16185(13) 0.0211(3) Uani 1 1 d . . . . .
H8 H 1.0468 0.5873 0.0965 0.025 Uiso 1 1 calc R . . . .
C7 C 1.08477(18) 0.66060(14) 0.27898(14) 0.0236(3) Uani 1 1 d . . . . .
H7 H 1.1916 0.7055 0.2915 0.028 Uiso 1 1 calc R . . . .

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 0.0168(4) 0.0183(5) 0.0221(5) 0.0008(4) 0.0082(4) 0.0017(4)
O2 0.0256(5) 0.0216(5) 0.0230(5) 0.0053(4) 0.0159(4) 0.0049(4)
N1 0.0170(5) 0.0212(6) 0.0161(5) 0.0004(4) 0.0077(4) 0.0005(4)
C3 0.0126(5) 0.0167(6) 0.0164(6) -0.0029(5) 0.0052(4) -0.0031(5)
C4 0.0149(6) 0.0141(6) 0.0188(6) 0.0028(5) 0.0068(5) 0.0026(5)
C2 0.0163(6) 0.0152(6) 0.0158(6) 0.0027(5) 0.0065(5) 0.0045(5)
C1 0.0149(6) 0.0168(6) 0.0173(6) -0.0002(5) 0.0071(5) 0.0016(5)
C9 0.0198(6) 0.0170(6) 0.0176(6) 0.0010(5) 0.0078(5) 0.0010(5)
C5 0.0202(6) 0.0190(6) 0.0203(6) -0.0014(5) 0.0089(5) 0.0016(5)
C6 0.0213(7) 0.0204(7) 0.0279(7) -0.0072(6) 0.0072(5) -0.0025(6)
C8 0.0217(7) 0.0191(6) 0.0273(7) 0.0030(5) 0.0145(6) 0.0010(5)
C7 0.0176(6) 0.0177(6) 0.0376(8) -0.0005(6) 0.0124(6) -0.0020(5)

_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 C3 1.2122(15) . ?
O2 H2 0.8200 . ?
O2 C3 1.3321(15) . ?
N1 C2 1.2566(16) . ?
N1 C1 1.5446(15) . ?
C3 C1 1.4872(18) . ?
C4 C2 1.4472(17) . ?
C4 C9 1.4026(17) . ?
C4 C5 1.3942(18) . ?
C2 C1 1.4625(17) . ?
C1 H1 0.9800 . ?
C9 H9 0.9300 . ?
C9 C8 1.3865(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.3904(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.3914(19) . ?
C7 H7 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
C3 O2 H2 109.5 . . ?
C2 N1 C1 61.94(8) . . ?
O1 C3 O2 124.67(12) . . ?
O1 C3 C1 123.87(11) . . ?
O2 C3 C1 111.46(11) . . ?
C9 C4 C2 119.37(11) . . ?
C5 C4 C2 119.77(11) . . ?
C5 C4 C9 120.85(12) . . ?
N1 C2 C4 143.07(12) . . ?
N1 C2 C1 68.75(9) . . ?
C4 C2 C1 148.08(11) . . ?
N1 C1 H1 118.7 . . ?
C3 C1 N1 114.38(10) . . ?
C3 C1 H1 118.7 . . ?
C2 C1 N1 49.31(7) . . ?
C2 C1 C3 118.45(11) . . ?
C2 C1 H1 118.7 . . ?
C4 C9 H9 120.5 . . ?
C8 C9 C4 118.96(12) . . ?
C8 C9 H9 120.5 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.32(12) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.19(13) . . ?
C7 C6 H6 119.9 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.51(12) . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 120.17(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?

_shelx_res_file                  
;
    pas5.res created by SHELXL-2014/7

TITL pas5_a.res in P2(1)/c
REM Old TITL CF solution in P21/c
REM SHELXT solution in P2(1)/c
REM R1 0.103, Rweak 0.192, Alpha 0.015, Orientation as input
REM Formula found by SHELXT: C9 N O2
CELL 0.71073 8.0481 9.7876 10.8529 90 111.525 90
ZERR 4 0.0009 0.0009 0.0013 0 0.013 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 36 28 4 8

L.S. 4
PLAN  25
BOND $H
list 4
fmap 2
acta
OMIT -4 57
REM <olex2.extras>
REM <HklSrc "%.\\pas5.hkl">
REM </olex2.extras>

WGHT    0.037900    0.217900
FVAR       0.86338
O1    4    0.610055    0.216401    0.386592    11.00000    0.01679    0.01834 =
         0.02212    0.00081    0.00818    0.00169
O2    4    0.411487    0.324314    0.454646    11.00000    0.02559    0.02155 =
         0.02303    0.00530    0.01586    0.00488
AFIX 147
H2    2    0.436946    0.263123    0.510100    11.00000   -1.50000
AFIX   0
N1    3    0.488642    0.374856    0.145485    11.00000    0.01701    0.02119 =
         0.01606    0.00037    0.00767    0.00047
C3    1    0.505020    0.308358    0.376676    11.00000    0.01265    0.01670 =
         0.01637   -0.00293    0.00516   -0.00309
C4    1    0.766260    0.526799    0.241410    11.00000    0.01491    0.01412 =
         0.01882    0.00280    0.00683    0.00259
C2    1    0.601474    0.454973    0.222309    11.00000    0.01627    0.01521 =
         0.01583    0.00272    0.00653    0.00454
C1    1    0.464175    0.417764    0.274745    11.00000    0.01492    0.01676 =
         0.01727   -0.00020    0.00713    0.00158
AFIX  13
H1    2    0.371518    0.484848    0.269732    11.00000   -1.20000
AFIX   0
C9    1    0.838303    0.522267    0.141783    11.00000    0.01982    0.01701 =
         0.01757    0.00104    0.00783    0.00099
AFIX  43
H9    2    0.780082    0.474828    0.063495    11.00000   -1.20000
AFIX   0
C5    1    0.852362    0.598212    0.358786    11.00000    0.02020    0.01904 =
         0.02027   -0.00136    0.00895    0.00162
AFIX  43
H5    2    0.803165    0.601474    0.424030    11.00000   -1.20000
AFIX   0
C6    1    1.012544    0.664504    0.377295    11.00000    0.02128    0.02040 =
         0.02789   -0.00724    0.00723   -0.00250
AFIX  43
H6    2    1.071541    0.711591    0.455665    11.00000   -1.20000
AFIX   0
C8    1    0.997684    0.589625    0.161849    11.00000    0.02166    0.01912 =
         0.02730    0.00296    0.01446    0.00101
AFIX  43
H8    2    1.046764    0.587349    0.096511    11.00000   -1.20000
AFIX   0
C7    1    1.084768    0.660602    0.278984    11.00000    0.01758    0.01769 =
         0.03755   -0.00046    0.01235   -0.00200
AFIX  43
H7    2    1.191566    0.705548    0.291544    11.00000   -1.20000
AFIX   0
HKLF 4

REM  pas5_a.res in P2(1)/c
REM R1 =  0.0409 for    1652 Fo > 4sig(Fo)  and  0.0512 for all    2004 data
REM    110 parameters refined using      0 restraints

END

WGHT      0.0379      0.2180

REM Highest difference peak  0.333,  deepest hole -0.210,  1-sigma level  0.049
Q1    1   0.4980  0.3762  0.3369  11.00000  0.05    0.33
Q2    1   0.7775  0.5540  0.1787  11.00000  0.05    0.25
Q3    1   0.6845  0.4938  0.2270  11.00000  0.05    0.25
Q4    1   0.9024  0.5818  0.1437  11.00000  0.05    0.24
Q5    1   1.0164  0.6437  0.2141  11.00000  0.05    0.23
Q6    1   0.8292  0.5045  0.2069  11.00000  0.05    0.23
Q7    1   0.8445  0.5304  0.3135  11.00000  0.05    0.23
Q8    1   0.9131  0.6575  0.3538  11.00000  0.05    0.21
Q9    1   0.7874  0.5859  0.2827  11.00000  0.05    0.21
Q10   1   0.5758  0.4477  0.2938  11.00000  0.05    0.17
Q11   1   1.0270  0.6790  0.3178  11.00000  0.05    0.17
Q12   1   0.7176  0.2406  0.3960  11.00000  0.05    0.16
Q13   1   0.9524  0.5304  0.1782  11.00000  0.05    0.15
Q14   1   0.7364  0.4316  0.0189  11.00000  0.05    0.15
Q15   1   0.5970  0.3867  0.1866  11.00000  0.05    0.15
Q16   1   0.8108  0.3948  0.3303  11.00000  0.05    0.15
Q17   1   0.4981  0.1872  0.3783  11.00000  0.05    0.15
Q18   1   0.7704  0.3035  0.3556  11.00000  0.05    0.14
Q19   1   0.2999  0.3777  0.4085  11.00000  0.05    0.14
Q20   1   0.7818  0.5686  0.4629  11.00000  0.05    0.14
Q21   1   0.6984  0.1200  0.4252  11.00000  0.05    0.14
Q22   1   1.0697  0.8540  0.2011  11.00000  0.05    0.13
Q23   1   1.2525  0.7088  0.3592  11.00000  0.05    0.13
Q24   1   1.2767  0.7759  0.2117  11.00000  0.05    0.13
Q25   1   0.6403  0.5356 -0.0216  11.00000  0.05    0.13
;
_shelx_res_checksum              68263
_olex2_submission_special_instructions 'No special instructions were received'
