#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:24:25 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288821 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247703.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_7247703
loop_
_publ_author_name
'Han, Wei'
'Chen, Yu-Lan'
'Tang, Xi'
'Zhou, Jie'
'Ma, Mengtao'
'Shen, Zhi-Liang'
'Chu, Xue-Qiang'
_publ_section_title
;
 Water-promoted defluorinative synthesis of fluoroalkylated
 1,5-diazapentadienes by using (NH4)2CO3 as an NH2 and NH source
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              9672
_journal_page_last               9679
_journal_paper_doi               10.1039/D3GC03717G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C13 H8 F7 N3'
_chemical_formula_sum            'C13 H8 F7 N3'
_chemical_formula_weight         339.22
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.132(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5372(11)
_cell_length_b                   11.7335(9)
_cell_length_c                   10.3893(9)
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      28.2740
_cell_measurement_theta_min      2.6640
_cell_volume                     1363.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (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      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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     -9.00  77.00   1.00    2.50    --   12.05  38.00-120.00   86
  2  ω    -57.00  39.00   1.00    2.50    --   12.05 -57.00  60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139191000
_diffrn_orient_matrix_UB_12      0.0556314000
_diffrn_orient_matrix_UB_13      -0.0179349000
_diffrn_orient_matrix_UB_21      -0.0463054000
_diffrn_orient_matrix_UB_22      -0.0034920000
_diffrn_orient_matrix_UB_23      -0.0591042000
_diffrn_orient_matrix_UB_31      -0.0410781000
_diffrn_orient_matrix_UB_32      0.0229764000
_diffrn_orient_matrix_UB_33      0.0340383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.515
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0395
_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)+(0.0560P)²+0.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1991
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc03717g2.cif
_cod_data_source_block           1023-1
_cod_depositor_comments
'Adding full bibliography for 7247703--7247704.cif.'
_cod_database_code               7247703
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8)
;
_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 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.736
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'
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
F1 F -0.01698(10) 0.49150(10) 0.78203(11) 0.0483(3) Uani 1 1 d . . . . .
F2 F 0.04930(10) 0.62780(8) 0.67885(10) 0.0454(3) Uani 1 1 d . . . . .
F3 F 0.18691(12) 0.47815(10) 0.96466(11) 0.0605(4) Uani 1 1 d . . . . .
F4 F 0.27376(10) 0.59982(11) 0.85918(13) 0.0619(4) Uani 1 1 d . . . . .
F5 F 0.02269(12) 0.64891(10) 0.98081(13) 0.0628(4) Uani 1 1 d . . . . .
F6 F 0.20775(14) 0.68172(13) 1.07520(14) 0.0879(5) Uani 1 1 d . . . . .
F7 F 0.12546(11) 0.76416(9) 0.89356(12) 0.0593(4) Uani 1 1 d . . . . .
N1 N 0.56039(16) 0.65288(13) 0.08559(16) 0.0467(4) Uani 1 1 d . . . . .
N2 N 0.25497(16) 0.30519(13) 0.51871(17) 0.0377(4) Uani 1 1 d . . . . .
H2A H 0.217(2) 0.2779(18) 0.576(2) 0.055(6) Uiso 1 1 d . . . . .
H2B H 0.3011(18) 0.2658(17) 0.4795(19) 0.044(6) Uiso 1 1 d . . . . .
N3 N 0.13184(15) 0.33768(12) 0.70635(16) 0.0396(4) Uani 1 1 d . . . . .
H3 H 0.0876(18) 0.3264(16) 0.764(2) 0.048(6) Uiso 1 1 d . . . . .
C1 C 0.33201(16) 0.41126(14) 0.30512(16) 0.0327(4) Uani 1 1 d . . . . .
H1 H 0.296497 0.338144 0.286562 0.039 Uiso 1 1 calc R U . . .
C2 C 0.39560(16) 0.45681(14) 0.22114(17) 0.0342(4) Uani 1 1 d . . . . .
H2 H 0.404808 0.414758 0.146129 0.041 Uiso 1 1 calc R U . . .
C3 C 0.44611(15) 0.56426(14) 0.24642(16) 0.0305(4) Uani 1 1 d . . . . .
C4 C 0.43207(15) 0.62546(14) 0.35601(17) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.465167 0.699718 0.372519 0.038 Uiso 1 1 calc R U . . .
C5 C 0.37036(15) 0.57864(13) 0.44046(16) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.362491 0.620367 0.516225 0.037 Uiso 1 1 calc R U . . .
C6 C 0.31898(14) 0.47052(13) 0.41659(16) 0.0278(4) Uani 1 1 d . . . . .
C7 C 0.25431(15) 0.41946(14) 0.51005(16) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.19718(16) 0.48610(14) 0.58268(17) 0.0321(4) Uani 1 1 d . . . . .
H8 H 0.197098 0.566126 0.568772 0.038 Uiso 1 1 calc R U . . .
C9 C 0.13749(15) 0.44397(14) 0.67815(16) 0.0310(4) Uani 1 1 d . . . . .
C10 C 0.08270(15) 0.53296(14) 0.75227(17) 0.0332(4) Uani 1 1 d . . . . .
C11 C 0.16810(17) 0.56947(16) 0.88357(18) 0.0404(5) Uani 1 1 d . . . . .
C12 C 0.1293(2) 0.66762(17) 0.9597(2) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.51059(17) 0.61292(15) 0.15718(17) 0.0353(4) 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 0.0033 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'
F F 0.0171 0.0103 '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'
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
H2A N2 H2B 125.5(19) . . ?
C7 N2 H2A 114.4(14) . . ?
C7 N2 H2B 119.2(13) . . ?
C9 N3 H3 111.6(13) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.08(16) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.80(16) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.84(15) . . ?
C2 C3 C13 119.84(15) . . ?
C4 C3 C13 120.30(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.99(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.93(15) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.34(15) . . ?
C1 C6 C7 121.06(15) . . ?
C5 C6 C7 120.58(14) . . ?
N2 C7 C6 116.75(14) . . ?
N2 C7 C8 122.07(15) . . ?
C8 C7 C6 121.18(15) . . ?
C7 C8 H8 117.7 . . ?
C7 C8 C9 124.52(15) . . ?
C9 C8 H8 117.7 . . ?
N3 C9 C8 123.65(16) . . ?
N3 C9 C10 119.94(15) . . ?
C8 C9 C10 116.37(14) . . ?
F1 C10 C9 110.49(14) . . ?
F1 C10 C11 107.11(14) . . ?
F2 C10 F1 106.51(14) . . ?
F2 C10 C9 112.06(13) . . ?
F2 C10 C11 107.73(14) . . ?
C9 C10 C11 112.63(14) . . ?
F3 C11 F4 108.16(15) . . ?
F3 C11 C10 107.70(15) . . ?
F3 C11 C12 107.39(16) . . ?
F4 C11 C10 108.61(15) . . ?
F4 C11 C12 106.91(16) . . ?
C12 C11 C10 117.74(16) . . ?
F5 C12 F6 109.23(18) . . ?
F5 C12 F7 108.40(16) . . ?
F5 C12 C11 111.36(17) . . ?
F6 C12 C11 109.97(17) . . ?
F7 C12 F6 107.02(18) . . ?
F7 C12 C11 110.74(17) . . ?
N1 C13 C3 178.9(2) . . ?
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
F1 C10 1.3522(19) . ?
F2 C10 1.3510(19) . ?
F3 C11 1.347(2) . ?
F4 C11 1.352(2) . ?
F5 C12 1.319(2) . ?
F6 C12 1.325(2) . ?
F7 C12 1.320(2) . ?
N1 C13 1.145(2) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.88(2) . ?
N2 C7 1.344(2) . ?
N3 H3 0.89(2) . ?
N3 C9 1.286(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 C4 1.389(2) . ?
C3 C13 1.441(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(2) . ?
C6 C7 1.487(2) . ?
C7 C8 1.363(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.427(2) . ?
C9 C10 1.523(2) . ?
C10 C11 1.536(3) . ?
C11 C12 1.525(3) . ?
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
F1 C10 C11 F3 56.52(18) . . . . ?
F1 C10 C11 F4 173.43(13) . . . . ?
F1 C10 C11 C12 -65.0(2) . . . . ?
F2 C10 C11 F3 170.76(13) . . . . ?
F2 C10 C11 F4 -72.33(17) . . . . ?
F2 C10 C11 C12 49.3(2) . . . . ?
F3 C11 C12 F5 -68.2(2) . . . . ?
F3 C11 C12 F6 53.1(2) . . . . ?
F3 C11 C12 F7 171.14(16) . . . . ?
F4 C11 C12 F5 175.96(16) . . . . ?
F4 C11 C12 F6 -62.8(2) . . . . ?
F4 C11 C12 F7 55.3(2) . . . . ?
N2 C7 C8 C9 2.8(3) . . . . ?
N3 C9 C10 F1 -34.5(2) . . . . ?
N3 C9 C10 F2 -153.13(16) . . . . ?
N3 C9 C10 C11 85.2(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C13 -178.76(16) . . . . ?
C1 C6 C7 N2 28.0(2) . . . . ?
C1 C6 C7 C8 -151.87(17) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -177.63(15) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 178.78(15) . . . . ?
C5 C6 C7 N2 -150.68(16) . . . . ?
C5 C6 C7 C8 29.5(2) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C6 C7 C8 C9 -177.33(16) . . . . ?
C7 C8 C9 N3 0.4(3) . . . . ?
C7 C8 C9 C10 177.97(16) . . . . ?
C8 C9 C10 F1 147.76(15) . . . . ?
C8 C9 C10 F2 29.2(2) . . . . ?
C8 C9 C10 C11 -92.50(18) . . . . ?
C9 C10 C11 F3 -65.16(19) . . . . ?
C9 C10 C11 F4 51.76(19) . . . . ?
C9 C10 C11 C12 173.35(16) . . . . ?
C10 C11 C12 F5 53.5(2) . . . . ?
C10 C11 C12 F6 174.71(17) . . . . ?
C10 C11 C12 F7 -67.2(2) . . . . ?
C13 C3 C4 C5 179.88(16) . . . . ?
