#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:58:55 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158420.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_7158420
loop_
_publ_author_name
'Camats, Marc'
'Favier, Isabelle'
'Mallet-Ladeira, Sonia'
'Pla, Daniel'
'Gómez, Montserrat'
_publ_section_title
;
 Understanding Cu(II)-based systems for C(sp³)-H bond
 functionalization: insights into the synthesis of aza-heterocycles.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              219
_journal_page_last               227
_journal_paper_doi               10.1039/d1ob02118d
_journal_volume                  20
_journal_year                    2021
_chemical_formula_moiety         'C10 H8 F N3'
_chemical_formula_sum            'C10 H8 F N3'
_chemical_formula_weight         189.19
_space_group_IT_number           72
_space_group_name_Hall           '-I 2 2c'
_space_group_name_H-M_alt        'I b a m'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      72
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_space_group_name_H-M   'I b a m'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2021-04-12 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8734(6)
_cell_length_b                   17.3509(7)
_cell_length_c                   6.6216(3)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      3.29
_cell_volume                     1823.71(13)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32011
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.987
_diffrn_reflns_theta_min         4.026
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0694P)²+0.3294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0
_reflns_number_gt                1819
_reflns_number_total             2099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02118d2.cif
_cod_data_source_block           6a
_cod_depositor_comments
'Adding full bibliography for 7158417--7158420.cif.'
_cod_database_code               7158420
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, 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
C1 C 0.90580(7) 0.43618(6) 0.5 0.0391(2) Uani 1 2 d S T P . .
C2 C 0.81053(6) 0.42887(5) 0.5 0.0336(2) Uani 1 2 d S T P . .
H2A H 0.787837 0.455353 0.620747 0.04 Uiso 0.5 1 calc R U P . .
H2B H 0.787837 0.455353 0.379253 0.04 Uiso 0.5 1 calc R U P . .
C3 C 0.78074(5) 0.34786(4) 0.5 0.02325(15) Uani 1 2 d S T P . .
C4 C 0.62617(6) 0.37753(6) 0.5 0.03142(19) Uani 1 2 d S T P . .
H4 H 0.632563 0.431968 0.5 0.038 Uiso 1 2 calc R U P . .
C5 C 0.54848(6) 0.34482(7) 0.5 0.0371(2) Uani 1 2 d S T P . .
H5 H 0.500056 0.376994 0.5 0.044 Uiso 1 2 calc R U P . .
C6 C 0.53798(6) 0.26305(7) 0.5 0.0367(2) Uani 1 2 d S T P . .
H6 H 0.483359 0.24066 0.5 0.044 Uiso 1 2 calc R U P . .
C7 C 0.60766(6) 0.21836(6) 0.5 0.02986(18) Uani 1 2 d S T P . .
C8 C 0.68958(5) 0.25003(5) 0.5 0.02305(15) Uani 1 2 d S T P . .
C9 C 0.77194(5) 0.22345(5) 0.5 0.02289(15) Uani 1 2 d S T P . .
C10 C 0.80051(6) 0.14617(5) 0.5 0.02821(17) Uani 1 2 d S T P . .
N1 N 0.82721(4) 0.28501(4) 0.5 0.02336(15) Uani 1 2 d S T P . .
N2 N 0.69581(4) 0.32954(4) 0.5 0.02344(15) Uani 1 2 d S T P . .
N3 N 0.82499(6) 0.08353(5) 0.5 0.0417(2) Uani 1 2 d S T P . .
F1 F 0.60360(5) 0.14077(4) 0.5 0.04310(19) Uani 1 2 d S T P . .
H1A H 0.9230(10) 0.4904(10) 0.5 0.046(4) Uiso 1 2 d S . P . .
H1B H 0.9313(8) 0.4088(7) 0.382(2) 0.062(4) Uiso 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 0 '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'
F F 0.0171 0.0103 '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
C2 C1 H1A 111.0(10) . . ?
C2 C1 H1B 111.4(8) . . ?
H1A C1 H1B 110.1(9) . . ?
C2 C1 H1B 111.4(8) . 10_556 ?
H1A C1 H1B 110.1(9) . 10_556 ?
H1B C1 H1B 102.7(15) . 10_556 ?
C3 C2 C1 113.39(8) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 N2 110.81(7) . . ?
N1 C3 C2 127.33(7) . . ?
N2 C3 C2 121.86(7) . . ?
C5 C4 N2 118.29(10) . . ?
C5 C4 H4 120.9 . . ?
N2 C4 H4 120.9 . . ?
C4 C5 C6 121.42(9) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 118.33(8) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
F1 C7 C6 122.29(9) . . ?
F1 C7 C8 115.64(8) . . ?
C6 C7 C8 122.07(9) . . ?
N2 C8 C9 105.33(7) . . ?
N2 C8 C7 117.00(8) . . ?
C9 C8 C7 137.67(8) . . ?
N1 C9 C8 109.97(7) . . ?
N1 C9 C10 121.92(7) . . ?
C8 C9 C10 128.11(7) . . ?
N3 C10 C9 179.00(10) . . ?
C3 N1 C9 106.53(7) . . ?
C8 N2 C4 122.89(7) . . ?
C8 N2 C3 107.37(7) . . ?
C4 N2 C3 129.74(8) . . ?
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
C1 C2 1.5175(14) . ?
C1 H1A 0.979(17) . ?
C1 H1B 0.998(13) . ?
C1 H1B 0.998(13) 10_556 ?
C2 C3 1.4831(12) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 N1 1.3165(10) . ?
C3 N2 1.3851(10) . ?
C4 C5 1.3575(13) . ?
C4 N2 1.3841(11) . ?
C4 H4 0.95 . ?
C5 C6 1.4285(17) . ?
C5 H5 0.95 . ?
C6 C7 1.3508(14) . ?
C6 H6 0.95 . ?
C7 F1 1.3479(11) . ?
C7 C8 1.4117(11) . ?
C8 N2 1.3831(11) . ?
C8 C9 1.3862(11) . ?
C9 N1 1.3822(10) . ?
C9 C10 1.4156(12) . ?
C10 N3 1.1542(12) . ?
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
C1 C2 C3 N1 0 . . . . ?
C1 C2 C3 N2 180 . . . . ?
N2 C4 C5 C6 0 . . . . ?
C4 C5 C6 C7 0 . . . . ?
C5 C6 C7 F1 180 . . . . ?
C5 C6 C7 C8 0 . . . . ?
F1 C7 C8 N2 180 . . . . ?
C6 C7 C8 N2 0 . . . . ?
F1 C7 C8 C9 0 . . . . ?
C6 C7 C8 C9 180 . . . . ?
N2 C8 C9 N1 0 . . . . ?
C7 C8 C9 N1 180 . . . . ?
N2 C8 C9 C10 180 . . . . ?
C7 C8 C9 C10 0 . . . . ?
N2 C3 N1 C9 0 . . . . ?
C2 C3 N1 C9 180 . . . . ?
C8 C9 N1 C3 0 . . . . ?
C10 C9 N1 C3 180 . . . . ?
C9 C8 N2 C4 180 . . . . ?
C7 C8 N2 C4 0 . . . . ?
C9 C8 N2 C3 0 . . . . ?
C7 C8 N2 C3 180 . . . . ?
C5 C4 N2 C8 0 . . . . ?
C5 C4 N2 C3 180 . . . . ?
N1 C3 N2 C8 0 . . . . ?
C2 C3 N2 C8 180 . . . . ?
N1 C3 N2 C4 180 . . . . ?
C2 C3 N2 C4 0 . . . . ?
