#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/12/7121270.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_7121270
loop_
_publ_author_name
'Tu, Daoquan'
'Luo, Jun'
'Jiang, Chao'
_publ_section_title
;
 Copper-mediated domino C-H iodination and nitration of indoles.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2514
_journal_page_last               2517
_journal_paper_doi               10.1039/c8cc00267c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C12 H6 F I N4 O2'
_chemical_formula_weight         384.11
_chemical_name_systematic
4-fluoro-3-iodo-2-nitro-1-(pyrimidin-2-yl)-1H-indole
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.387(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.618(5)
_cell_length_b                   9.329(3)
_cell_length_c                   8.150(3)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.45
_cell_volume                     1263.5(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6827
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.644
_diffrn_reflns_theta_min         1.225
_exptl_absorpt_coefficient_mu    2.554
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_refine_diff_density_max         1.118
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0484
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2271
_reflns_number_total             2920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc00267c2.cif
_cod_data_source_block           www_a
_cod_depositor_comments          'Adding full bibliography for 7121270.cif.'
_cod_database_code               7121270
_shelx_shelxl_version_number     2014/7
_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.
;
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
I1 I 0.17602(3) 0.28216(4) 0.53376(5) 0.0607(2) Uani 1 1 d . .
F1 F 0.0423(2) 0.5206(4) 0.6684(4) 0.0633(10) Uani 1 1 d . .
N2 N 0.2653(2) 0.6923(4) 0.3895(5) 0.0339(8) Uani 1 1 d . .
O1 O 0.3456(2) 0.5064(5) 0.1768(5) 0.0545(10) Uani 1 1 d . .
N1 N 0.3267(2) 0.4631(5) 0.3125(5) 0.0430(10) Uani 1 1 d . .
N3 N 0.3143(2) 0.9092(5) 0.2948(5) 0.0395(9) Uani 1 1 d . .
O2 O 0.3525(3) 0.3543(5) 0.3752(6) 0.0655(12) Uani 1 1 d . .
N4 N 0.4039(2) 0.7274(5) 0.3918(6) 0.0447(10) Uani 1 1 d . .
C1 C 0.1958(2) 0.7394(5) 0.4710(6) 0.0302(9) Uani 1 1 d . .
C7 C 0.2026(3) 0.4929(5) 0.4865(5) 0.0337(9) Uani 1 1 d . .
C9 C 0.3327(3) 0.7826(5) 0.3553(6) 0.0333(9) Uani 1 1 d . .
C2 C 0.1547(2) 0.6153(5) 0.5287(5) 0.0307(9) Uani 1 1 d . .
C8 C 0.2681(2) 0.5457(5) 0.4045(5) 0.0339(9) Uani 1 1 d . .
C3 C 0.0825(3) 0.6356(6) 0.6121(6) 0.0408(11) Uani 1 1 d . .
C10 C 0.3781(3) 0.9958(6) 0.2669(7) 0.0489(13) Uani 1 1 d . .
H10 H 0.3694 1.0875 0.2254 0.059 Uiso 1 1 calc R U
C4 C 0.1661(3) 0.8762(6) 0.4969(7) 0.0437(11) Uani 1 1 d . .
H4 H 0.1921 0.9568 0.4559 0.052 Uiso 1 1 calc R U
C5 C 0.0533(3) 0.7705(7) 0.6398(7) 0.0495(14) Uani 1 1 d . .
H5 H 0.0049 0.7829 0.6943 0.059 Uiso 1 1 calc R U
C6 C 0.0959(3) 0.8873(6) 0.5868(7) 0.0468(12) Uani 1 1 d . .
H6 H 0.0768 0.9782 0.6123 0.056 Uiso 1 1 calc R U
C12 C 0.4657(3) 0.8159(7) 0.3605(8) 0.0553(14) Uani 1 1 d . .
H12 H 0.5177 0.7838 0.3818 0.066 Uiso 1 1 calc R U
C11 C 0.4557(3) 0.9509(7) 0.2987(7) 0.0535(14) Uani 1 1 d . .
H11 H 0.4995 1.0102 0.2789 0.064 Uiso 1 1 calc R U
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C8 N2 C1 107.2(4)
C8 N2 C9 125.3(4)
C1 N2 C9 123.7(4)
O2 N1 O1 124.5(4)
O2 N1 C8 117.5(4)
O1 N1 C8 118.0(4)
C9 N3 C10 114.8(4)
C9 N4 C12 113.7(5)
C4 C1 N2 130.9(4)
C4 C1 C2 121.7(4)
N2 C1 C2 107.4(4)
C8 C7 C2 105.9(4)
C8 C7 I1 127.5(3)
C2 C7 I1 126.6(3)
N3 C9 N4 129.8(4)
N3 C9 N2 114.9(4)
N4 C9 N2 115.3(4)
C3 C2 C1 117.8(4)
C3 C2 C7 134.8(4)
C1 C2 C7 107.4(4)
C7 C8 N2 112.0(4)
C7 C8 N1 126.7(4)
N2 C8 N1 120.2(4)
F1 C3 C5 120.0(4)
F1 C3 C2 119.2(5)
C5 C3 C2 120.8(5)
N3 C10 C11 121.2(5)
N3 C10 H10 119.4
C11 C10 H10 119.4
C1 C4 C6 116.8(5)
C1 C4 H4 121.6
C6 C4 H4 121.6
C3 C5 C6 119.7(4)
C3 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C4 123.0(5)
C5 C6 H6 118.5
C4 C6 H6 118.5
N4 C12 C11 123.0(5)
N4 C12 H12 118.5
C11 C12 H12 118.5
C12 C11 C10 117.5(5)
C12 C11 H11 121.3
C10 C11 H11 121.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C7 2.052(4)
F1 C3 1.346(6)
N2 C8 1.374(6)
N2 C1 1.407(5)
N2 C9 1.431(5)
O1 N1 1.221(6)
N1 O2 1.213(6)
N1 C8 1.455(6)
N3 C9 1.315(6)
N3 C10 1.353(6)
N4 C9 1.322(6)
N4 C12 1.344(7)
C1 C4 1.385(7)
C1 C2 1.426(6)
C7 C8 1.371(6)
C7 C2 1.436(6)
C2 C3 1.395(6)
C3 C5 1.368(8)
C10 C11 1.379(8)
C10 H10 0.9300
C4 C6 1.386(6)
C4 H4 0.9300
C5 C6 1.370(8)
C5 H5 0.9300
C6 H6 0.9300
C12 C11 1.366(9)
C12 H12 0.9300
C11 H11 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188436
