#------------------------------------------------------------------------------
#$Date: 2024-09-20 02:49:46 +0200 (Fri 20 de Sep de 2024) $
#$Revision: 294815 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/01/7160146.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160146
loop_
_publ_author_name
'Paramonova, Polina'
'Lebedev, Rodion'
'Sokolov, Alexander'
'Dar'in, Dmitry'
'Kanov, Evgeny'
'Murtazina, Ramilya'
'Gainetdinov, Raul'
'Kalinin, Stanislav'
'Bakulina, Olga'
_publ_section_title
;
 Azide-based in situ preparation of fused heterocyclic imines and their
 multicomponent reactions
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D4OB01321B
_journal_year                    2024
_chemical_formula_moiety         '0.667(C2 F3 O2), 0.667(C7 H10 N3 O2)'
_chemical_formula_sum            'C6 H6.67 F2 N2 O2.67'
_chemical_formula_weight         187.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-06-03 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.670(3)
_cell_angle_beta                 96.664(3)
_cell_angle_gamma                95.213(3)
_cell_formula_units_Z            3
_cell_length_a                   6.2237(2)
_cell_length_b                   8.6358(3)
_cell_length_c                   10.4449(4)
_cell_measurement_reflns_used    5184
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.8260
_cell_measurement_theta_min      4.2450
_cell_volume                     555.14(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     97.00 177.00   0.50    0.20    --  113.25  61.00 120.00  160
  2  ω    132.00 157.00   0.50    0.20    --  113.25  82.00 -14.00   50
  3  ω    102.00 173.00   0.50    0.20    --  113.25  45.00-150.00  142
  4  ω     74.00 110.00   0.50    0.05    --   47.38 125.00 -90.00   72
  5  ω     77.00 116.00   0.50    0.05    --   47.38 125.00-180.00   78
  6  ω    -65.00 -35.00   0.50    0.20    -- -106.00  61.00-180.00   60
  7  ω    -64.00 -38.00   0.50    0.20    -- -106.00  61.00-150.00   52
  8  ω    -17.00  27.00   0.50    0.05    --  -47.38  19.00-120.00   88
  9  ω    -25.00  26.00   0.50    0.05    --  -47.38  19.00 -60.00  102
 10  ω    -71.00 -45.00   0.50    0.20    -- -106.00  61.00 150.00   52
 11  ω    -40.00  25.00   0.50    0.05    --  -47.38  37.00 150.00  130
 12  ω     50.00 105.00   0.50    0.20    --  113.25 -77.00 -30.00  110
 13  ω     69.00  94.00   0.50    0.20    --  113.25 -77.00 -60.00   50
 14  ω     43.00  69.00   0.50    0.20    --  113.25 -61.00-150.00   52
 15  ω    -17.00  23.00   0.50    0.05    --   47.38 -19.00 -30.00   80
 16  ω     47.00  94.00   0.50    0.20    --  113.25 -77.00  60.00   94
 17  ω     45.00  71.00   0.50    0.20    --  113.25 -61.00   0.00   52
 18  ω     42.00  69.00   0.50    0.20    --  113.25 -61.00 -60.00   54
 19  ω     45.00  71.00   0.50    0.20    --  113.25 -82.00-136.00   52
 20  ω     70.00 109.00   0.50    0.20    --  113.25-125.00-120.00   78
 21  ω     42.00 109.00   0.50    0.20    --  113.25-125.00 -60.00  134
 22  ω     55.00  80.00   0.50    0.20    --  113.25-125.00  90.00   50
 23  ω     72.00  97.00   0.50    0.20    --  113.25 -94.00 150.00   50
 24  ω     78.00 104.00   0.50    0.20    --  113.25 -94.00 120.00   52
 25  ω     26.00  63.00   0.50    0.05    --   47.38 -82.00-136.00   74
 26  ω     -9.00  17.00   0.50    0.05    --   47.38 -82.00-136.00   52
 27  ω   -167.00-135.00   0.50    0.20    -- -106.00 -94.00 -30.00   64
 28  ω   -126.00 -85.00   0.50    0.20    -- -106.00 -94.00 -30.00   82
 29  ω   -175.00-126.00   0.50    0.20    -- -106.00 -45.00 -60.00   98
 30  ω   -164.00-138.00   0.50    0.20    -- -106.00 -45.00 -90.00   52
 31  ω   -132.00-106.00   0.50    0.20    -- -106.00 -45.00 -90.00   52
 32  ω   -160.00 -82.00   0.50    0.20    -- -106.00 -82.00-136.00  156
 33  ω   -177.00-146.00   0.50    0.20    -- -106.00 -15.00   0.00   62
 34  ω   -134.00 -99.00   0.50    0.20    -- -106.00 -15.00   0.00   70
 35  ω    -80.00 -52.00   0.50    0.20    -- -106.00  82.00 -14.00   56
 36  ω    -70.00 -44.00   0.50    0.20    -- -106.00 125.00  30.00   52
 37  ω   -105.00 -76.00   0.50    0.20    -- -106.00 125.00  30.00   58
 38  ω   -126.00-101.00   0.50    0.20    -- -106.00 145.00 -33.06   50
 39  ω   -101.00 -55.00   0.50    0.20    -- -106.00 125.00 -30.00   92
 40  ω    -79.00 -40.00   0.50    0.20    -- -106.00 125.00 -90.00   78
 41  ω   -112.00 -69.00   0.50    0.20    -- -106.00 125.00-120.00   86
 42  ω   -109.00 -83.00   0.50    0.20    -- -106.00 125.00 -90.00   52
 43  ω    -66.00  23.00   0.50    0.05    --  -47.38  82.00 -14.00  178
 44  ω    -70.00 -34.00   0.50    0.20    -- -106.00 125.00 120.00   72
 45  ω   -112.00 -85.00   0.50    0.20    -- -106.00 125.00 120.00   54
 46  ω   -107.00 -73.00   0.50    0.20    -- -106.00 107.00  86.79   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1074562000
_diffrn_orient_matrix_UB_12      -0.1599669000
_diffrn_orient_matrix_UB_13      0.0332317000
_diffrn_orient_matrix_UB_21      -0.1589704000
_diffrn_orient_matrix_UB_22      0.0003326000
_diffrn_orient_matrix_UB_23      -0.1245570000
_diffrn_orient_matrix_UB_31      0.1607145000
_diffrn_orient_matrix_UB_32      -0.0807190000
_diffrn_orient_matrix_UB_33      -0.0737821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.344
_diffrn_reflns_theta_min         4.263
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.682
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_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     172
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0321
_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)+(0.0427P)²+0.2591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2204
_reflns_number_total             2297
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01321b2.cif
_cod_data_source_block           048-010_pps-102
_cod_database_code               7160146
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C7 H9 N3 O2'
_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.
;
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.759
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.11
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N009(H00A,H00B), C00G(H00D,H00E), C00H(H00G,H00H), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00F(H00F)
;
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.717
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
F001 F 1.03725(13) 0.16466(11) 0.74815(7) 0.0303(2) Uani 1 1 d . . . . .
F002 F 1.27895(12) 0.18846(10) 0.61698(7) 0.0269(2) Uani 1 1 d . . . . .
F003 F 1.08867(15) 0.37796(10) 0.64797(9) 0.0360(2) Uani 1 1 d . . . . .
O004 O 0.71677(13) 0.14304(10) 0.55203(8) 0.01746(19) Uani 1 1 d . . . . .
O005 O 0.97054(13) 0.15639(10) 0.41423(8) 0.01799(19) Uani 1 1 d . . . . .
O006 O 0.17023(14) 0.65534(10) -0.14240(8) 0.01803(19) Uani 1 1 d . . . . .
O007 O 0.26627(16) 0.81400(10) 0.02167(9) 0.0226(2) Uani 1 1 d . . . . .
N008 N 0.30608(15) 0.31485(11) 0.11469(9) 0.0127(2) Uani 1 1 d . . . . .
N009 N 0.39864(16) 0.17577(11) 0.35304(9) 0.0143(2) Uani 1 1 d . . . . .
H00A H 0.257120 0.160028 0.367770 0.017 Uiso 1 1 calc R U . . .
H00B H 0.481222 0.136698 0.420547 0.017 Uiso 1 1 calc R U . . .
N00A N 0.23381(15) 0.68104(11) -0.02702(10) 0.0150(2) Uani 1 1 d . . . . .
C00B C 0.24543(17) 0.40048(13) 0.01138(11) 0.0130(2) Uani 1 1 d . . . . .
H00C H 0.195179 0.362833 -0.073649 0.016 Uiso 1 1 calc R U . . .
C00C C 0.90514(18) 0.16604(13) 0.52140(11) 0.0143(2) Uani 1 1 d . . . . .
C00D C 0.27116(18) 0.55336(13) 0.05422(11) 0.0133(2) Uani 1 1 d . . . . .
C00E C 0.36663(18) 0.41105(13) 0.22203(11) 0.0135(2) Uani 1 1 d . . . . .
C00F C 0.34711(18) 0.56185(13) 0.18735(11) 0.0147(2) Uani 1 1 d . . . . .
H00F H 0.377881 0.652584 0.241028 0.018 Uiso 1 1 calc R U . . .
C00G C 0.42829(19) 0.09050(13) 0.23199(11) 0.0151(2) Uani 1 1 d . . . . .
H00D H 0.396779 -0.022718 0.242792 0.018 Uiso 1 1 calc R U . . .
H00E H 0.580660 0.110225 0.213410 0.018 Uiso 1 1 calc R U . . .
C00H C 0.27630(19) 0.14478(13) 0.12075(11) 0.0151(2) Uani 1 1 d . . . . .
H00G H 0.307576 0.097757 0.038811 0.018 Uiso 1 1 calc R U . . .
H00H H 0.123881 0.111161 0.133116 0.018 Uiso 1 1 calc R U . . .
C00I C 0.46072(19) 0.34619(13) 0.34602(11) 0.0164(2) Uani 1 1 d . . . . .
H00I H 0.621044 0.365408 0.354349 0.020 Uiso 1 1 calc R U . . .
H00J H 0.408979 0.400533 0.418943 0.020 Uiso 1 1 calc R U . . .
C00J C 1.0789(2) 0.22286(15) 0.63493(12) 0.0194(3) Uani 1 1 d . . . . .
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'
F F 0.0727 0.0534 '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'
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
C00B N008 C00E 109.93(9) . . ?
C00B N008 C00H 125.86(10) . . ?
C00E N008 C00H 123.34(9) . . ?
H00A N009 H00B 107.9 . . ?
C00G N009 H00A 109.2 . . ?
C00G N009 H00B 109.2 . . ?
C00I N009 H00A 109.2 . . ?
C00I N009 H00B 109.2 . . ?
C00I N009 C00G 112.11(9) . . ?
O006 N00A O007 122.95(10) . . ?
O006 N00A C00D 118.90(10) . . ?
O007 N00A C00D 118.15(10) . . ?
N008 C00B H00C 126.9 . . ?
N008 C00B C00D 106.20(10) . . ?
C00D C00B H00C 126.9 . . ?
O004 C00C C00J 114.09(10) . . ?
O005 C00C O004 129.73(11) . . ?
O005 C00C C00J 116.11(10) . . ?
C00B C00D N00A 123.73(10) . . ?
C00B C00D C00F 109.93(10) . . ?
C00F C00D N00A 126.29(10) . . ?
N008 C00E C00I 120.34(10) . . ?
C00F C00E N008 108.90(10) . . ?
C00F C00E C00I 130.36(11) . . ?
C00D C00F H00F 127.5 . . ?
C00E C00F C00D 105.04(10) . . ?
C00E C00F H00F 127.5 . . ?
N009 C00G H00D 109.7 . . ?
N009 C00G H00E 109.7 . . ?
N009 C00G C00H 109.62(9) . . ?
H00D C00G H00E 108.2 . . ?
C00H C00G H00D 109.7 . . ?
C00H C00G H00E 109.7 . . ?
N008 C00H C00G 109.51(9) . . ?
N008 C00H H00G 109.8 . . ?
N008 C00H H00H 109.8 . . ?
C00G C00H H00G 109.8 . . ?
C00G C00H H00H 109.8 . . ?
H00G C00H H00H 108.2 . . ?
N009 C00I C00E 111.78(9) . . ?
N009 C00I H00I 109.3 . . ?
N009 C00I H00J 109.3 . . ?
C00E C00I H00I 109.3 . . ?
C00E C00I H00J 109.3 . . ?
H00I C00I H00J 107.9 . . ?
F001 C00J F002 106.87(11) . . ?
F001 C00J F003 106.77(10) . . ?
F001 C00J C00C 113.46(10) . . ?
F002 C00J F003 106.58(10) . . ?
F002 C00J C00C 112.91(10) . . ?
F003 C00J C00C 109.83(10) . . ?
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
F001 C00J 1.3340(15) . ?
F002 C00J 1.3395(14) . ?
F003 C00J 1.3398(15) . ?
O004 C00C 1.2500(14) . ?
O005 C00C 1.2390(15) . ?
O006 N00A 1.2351(14) . ?
O007 N00A 1.2402(14) . ?
N008 C00B 1.3523(14) . ?
N008 C00E 1.3829(14) . ?
N008 C00H 1.4665(14) . ?
N009 H00A 0.9100 . ?
N009 H00B 0.9100 . ?
N009 C00G 1.4940(14) . ?
N009 C00I 1.4922(14) . ?
N00A C00D 1.4186(15) . ?
C00B H00C 0.9500 . ?
C00B C00D 1.3784(16) . ?
C00C C00J 1.5519(16) . ?
C00D C00F 1.4147(16) . ?
C00E C00F 1.3680(16) . ?
C00E C00I 1.4948(16) . ?
C00F H00F 0.9500 . ?
C00G H00D 0.9900 . ?
C00G H00E 0.9900 . ?
C00G C00H 1.5175(16) . ?
C00H H00G 0.9900 . ?
C00H H00H 0.9900 . ?
C00I H00I 0.9900 . ?
C00I H00J 0.9900 . ?
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
O004 C00C C00J F001 33.12(15) . . . . ?
O004 C00C C00J F002 154.91(10) . . . . ?
O004 C00C C00J F003 -86.28(12) . . . . ?
O005 C00C C00J F001 -149.73(11) . . . . ?
O005 C00C C00J F002 -27.94(15) . . . . ?
O005 C00C C00J F003 90.86(12) . . . . ?
O006 N00A C00D C00B 1.58(16) . . . . ?
O006 N00A C00D C00F 178.88(10) . . . . ?
O007 N00A C00D C00B -178.61(10) . . . . ?
O007 N00A C00D C00F -1.31(17) . . . . ?
N008 C00B C00D N00A 177.02(10) . . . . ?
N008 C00B C00D C00F -0.67(13) . . . . ?
N008 C00E C00F C00D 0.22(12) . . . . ?
N008 C00E C00I N009 -22.52(15) . . . . ?
N009 C00G C00H N008 52.82(12) . . . . ?
N00A C00D C00F C00E -177.34(10) . . . . ?
C00B N008 C00E C00F -0.66(13) . . . . ?
C00B N008 C00E C00I -174.14(10) . . . . ?
C00B N008 C00H C00G 161.01(10) . . . . ?
C00B C00D C00F C00E 0.28(13) . . . . ?
C00E N008 C00B C00D 0.81(12) . . . . ?
C00E N008 C00H C00G -30.71(14) . . . . ?
C00F C00E C00I N009 165.58(11) . . . . ?
C00G N009 C00I C00E 46.63(13) . . . . ?
C00H N008 C00B C00D 170.40(10) . . . . ?
C00H N008 C00E C00F -170.57(10) . . . . ?
C00H N008 C00E C00I 15.95(16) . . . . ?
C00I N009 C00G C00H -63.87(12) . . . . ?
C00I C00E C00F C00D 172.83(11) . . . . ?
