Non-natural 2H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity
Sakharov, Pavel A.; Koronatov, Alexander N.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; Glukharev, Artem G.; Rogacheva, Elizaveta V.; Kraeva, Liudmila A.; Sharoyko, Vladimir V.; Tennikova, Tatiana B.; Rostovskii, Nikolai V.; RSC Advances 9 (2019) 37901–; doi:10.1039/C9RA09345A

data_7235255
_publ_section_title
;
 Non-natural 2H-azirine-2-carboxylic acids: an expedient synthesis and
 antimicrobial activity
;
_journal_issue                   65
_journal_name_full               'RSC Advances'
_journal_page_first              37901
_journal_paper_doi               10.1039/C9RA09345A
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C9 H7 N O2'
_chemical_formula_sum            'C9 H7 N O2'
_chemical_formula_weight         161.16
_chemical_melting_point          379.0(10)
_chemical_name_systematic        '3-phenyl-2H-azirine-2-carboxylic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc23ntwh
_audit_creation_date             2019-08-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-09-28 deposited with the CCDC.	2019-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.525(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0481(9)
_cell_length_b                   9.7876(9)
_cell_length_c                   10.8529(13)
_cell_measurement_reflns_used    1443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6800
_cell_measurement_theta_min      2.8980
_cell_volume                     795.28(17)
_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)'
_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
;
  1 omega  -14.00   12.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -19.0000  -60.0000 26

  2 omega  -11.00   15.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000 -120.0000 26

  3 omega  -98.00  -35.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000    0.0000 63

  4 omega  -17.00    9.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   90.0000 26

  5 omega   -2.00   92.00   1.0000    3.3300
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000  -60.0000 94

  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       '\w 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_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_source                   'Enhance (Mo) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_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
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_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_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0409
_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/[\s^2^(Fo^2^)+(0.0379P)^2^+0.2179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1652
_reflns_number_total             2004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra09345a2.cif
_cod_data_source_block           pas5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '378-380' was changed to
'379.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        795.28(16)
_cod_database_code               7235255
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C9 N O2'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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)
;
_shelx_res_checksum              68263
_olex2_submission_special_instructions 'No special instructions were received'