1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the synthesis of pyrrole-containing heterocycles.
Galenko, Ekaterina E.; Shakirova, Firuza M.; Bodunov, Vladimir A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Organic & biomolecular chemistry 18 (2020) 2283–2296; doi:10.1039/d0ob00206b

data_7157371
_publ_section_title
;
 1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the
 synthesis of pyrrole-containing heterocycles.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2283
_journal_page_last               2296
_journal_paper_doi               10.1039/d0ob00206b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H15 Br N4 O2'
_chemical_formula_sum            'C20 H15 Br N4 O2'
_chemical_formula_weight         423.27
_chemical_melting_point          482.5(5)
_chemical_name_common            pyrrole
_chemical_name_systematic
1-(5-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-4-(4-bromophenyl)-2-methyl-1H-pyrrol-3-yl)ethan-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.8840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.09300(10)
_cell_length_b                   13.15410(10)
_cell_length_c                   16.98630(10)
_cell_measurement_reflns_used    10691
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9960
_cell_measurement_theta_min      5.7410
_cell_volume                     3542.44(4)
_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      100.01(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24540
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.472
_diffrn_reflns_theta_min         3.496
_exptl_absorpt_coefficient_mu    3.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysPlisPro 1.171.38.616 (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_preparation       'slow evaporation of acetonitrile'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0327
_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/[\s^2^(Fo^2^)+(0.0486P)^2^+2.2667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6525
_reflns_number_total             7008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00206b2.cif
_cod_data_source_block           7060-11415
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '482-483' was changed to
'482.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157371.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C20 H15 Br N4 O2)'
_cod_original_formula_sum        'C40 H30 Br2 N8 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     846.54
_cod_database_code               7157371
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.729
_shelx_estimated_absorpt_t_min   0.487
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1(H1), C10A(H10A), C9A(H9A), C13A(H13A), C16A(H16A), C12A(H12A),
 C13(H13), C9(H9), C19(H19), C12(H12), C10(H10), C19A(H19A), C18A(H18A),
 C16(H16), C17A(H17A), C18(H18), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1B,H1C,H1D), C1A(H1AA,H1AB,H1AC), C5(H5A,H5B,H5C), C5A(H5AA,H5AB,H5AC)
;
_shelx_res_checksum              51667
_olex2_submission_special_instructions 'No special instructions were received'