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#$Date: 2020-08-04 15:33:06 +0300 (Tue, 04 Aug 2020) $
#$Revision: 254788 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/70/7127002.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_7127002
loop_
_publ_author_name
'Zhang, Dong'
'Fang, Zheng'
'Cai, Jinlin'
'Liu, Chengkou'
'He, Wei'
'Duan, Jindian'
'Qin, Ning'
'Yang, Zhao'
'Guo, Kai'
_publ_section_title
;
 The copper(ii)-catalyzed and oxidant-promoted regioselective C-2
 difluoromethylation of indoles and pyrroles.
;
_journal_issue                   58
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8119
_journal_page_last               8122
_journal_paper_doi               10.1039/d0cc03345f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C15 H11 F2 N3 O2'
_chemical_formula_weight         303.27
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                99.54(3)
_cell_angle_beta                 107.52(3)
_cell_angle_gamma                109.15(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7930(16)
_cell_length_b                   9.7180(19)
_cell_length_c                   10.297(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      9
_cell_volume                     671.5(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.391
_diffrn_reflns_theta_min         2.170
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0571
_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+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1868
_reflns_number_total             2474
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03345f2.cif
_cod_data_source_block           X
_cod_original_cell_volume        671.5(3)
_cod_database_code               7127002
_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.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.988
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
N1 N 0.4808(3) 0.7694(2) 0.32171(19) 0.0435(5) Uani 1 1 d . . . . .
F1 F 0.6680(3) 0.8641(2) 0.08781(17) 0.0766(5) Uani 1 1 d . . . . .
O1 O 0.8761(3) 1.2074(2) 0.3385(2) 0.0735(6) Uani 1 1 d . . . . .
C1 C 0.5452(3) 0.7963(2) 0.4695(2) 0.0424(5) Uani 1 1 d . . . . .
F2 F 0.3717(2) 0.84289(18) 0.06052(15) 0.0687(5) Uani 1 1 d . . . . .
O2 O 0.9918(2) 1.22557(18) 0.56961(18) 0.0563(5) Uani 1 1 d . . . . .
N2 N 0.1867(3) 0.5571(2) 0.2473(2) 0.0530(5) Uani 1 1 d . . . . .
C2 C 0.4799(4) 0.7024(3) 0.5477(3) 0.0525(6) Uani 1 1 d . . . . .
H2B H 0.3763 0.6072 0.5035 0.063 Uiso 1 1 calc R U . . .
N3 N 0.3976(3) 0.5743(2) 0.1201(2) 0.0508(5) Uani 1 1 d . . . . .
C3 C 0.5747(4) 0.7561(3) 0.6929(3) 0.0596(7) Uani 1 1 d . . . . .
H3B H 0.5335 0.6962 0.7482 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7303(4) 0.8972(3) 0.7594(3) 0.0607(7) Uani 1 1 d . . . . .
H4A H 0.7914 0.9295 0.8582 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7962(4) 0.9903(3) 0.6829(2) 0.0521(6) Uani 1 1 d . . . . .
H5A H 0.9006 1.0849 0.7287 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7028(3) 0.9398(2) 0.5343(2) 0.0410(5) Uani 1 1 d . . . . .
C7 C 0.7295(3) 1.0019(2) 0.4206(2) 0.0416(5) Uani 1 1 d . . . . .
C8 C 0.5959(3) 0.8963(2) 0.2949(2) 0.0423(5) Uani 1 1 d . . . . .
C9 C 0.8700(3) 1.1536(3) 0.4345(3) 0.0475(6) Uani 1 1 d . . . . .
C10 C 1.1355(4) 1.3762(3) 0.5972(3) 0.0671(8) Uani 1 1 d . . . . .
H10A H 1.2152 1.4175 0.6972 0.101 Uiso 1 1 calc R U . . .
H10B H 1.2173 1.3711 0.5446 0.101 Uiso 1 1 calc R U . . .
H10C H 1.0698 1.4405 0.5681 0.101 Uiso 1 1 calc R U . . .
C11 C 0.5632(4) 0.9184(3) 0.1505(2) 0.0528(6) Uani 1 1 d . . . . .
H11A H 0.6034 1.0274 0.1597 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3461(3) 0.6259(2) 0.2223(2) 0.0426(5) Uani 1 1 d . . . . .
C13 C 0.0669(4) 0.4192(3) 0.1570(3) 0.0570(7) Uani 1 1 d . . . . .
H13A H -0.0453 0.3645 0.1710 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1020(4) 0.3548(3) 0.0447(3) 0.0567(6) Uani 1 1 d . . . . .
H14A H 0.0154 0.2592 -0.0183 0.068 Uiso 1 1 calc R U . . .
C15 C 0.2690(4) 0.4369(3) 0.0296(3) 0.0559(6) Uani 1 1 d . . . . .
H15A H 0.2957 0.3963 -0.0467 0.067 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'
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
C8 N1 C1 107.82(18) . . ?
C8 N1 C12 127.74(18) . . ?
C1 N1 C12 123.55(18) . . ?
C2 C1 N1 129.4(2) . . ?
C2 C1 C6 122.3(2) . . ?
N1 C1 C6 108.30(18) . . ?
C9 O2 C10 116.3(2) . . ?
C12 N2 C13 114.8(2) . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2B 121.5 . . ?
C1 C2 H2B 121.5 . . ?
C12 N3 C15 114.9(2) . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3B 119.1 . . ?
C4 C3 H3B 119.1 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 134.7(2) . . ?
C1 C6 C7 106.44(19) . . ?
C8 C7 C6 107.75(19) . . ?
C8 C7 C9 125.1(2) . . ?
C6 C7 C9 127.2(2) . . ?
C7 C8 N1 109.65(18) . . ?
C7 C8 C11 125.5(2) . . ?
N1 C8 C11 124.6(2) . . ?
O1 C9 O2 123.5(2) . . ?
O1 C9 C7 125.5(2) . . ?
O2 C9 C7 111.0(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 C11 F1 106.3(2) . . ?
F2 C11 C8 111.9(2) . . ?
F1 C11 C8 111.5(2) . . ?
F2 C11 H11A 109.0 . . ?
F1 C11 H11A 109.0 . . ?
C8 C11 H11A 109.0 . . ?
N3 C12 N2 127.9(2) . . ?
N3 C12 N1 116.3(2) . . ?
N2 C12 N1 115.7(2) . . ?
N2 C13 C14 122.8(2) . . ?
N2 C13 H13A 118.6 . . ?
C14 C13 H13A 118.6 . . ?
C15 C14 C13 116.8(2) . . ?
C15 C14 H14A 121.6 . . ?
C13 C14 H14A 121.6 . . ?
N3 C15 C14 122.8(2) . . ?
N3 C15 H15A 118.6 . . ?
C14 C15 H15A 118.6 . . ?
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
N1 C8 1.392(3) . ?
N1 C1 1.400(3) . ?
N1 C12 1.419(3) . ?
F1 C11 1.360(3) . ?
O1 C9 1.199(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.404(3) . ?
F2 C11 1.359(3) . ?
O2 C9 1.332(3) . ?
O2 C10 1.440(3) . ?
N2 C12 1.328(3) . ?
N2 C13 1.332(3) . ?
C2 C3 1.370(4) . ?
C2 H2B 0.9300 . ?
N3 C12 1.316(3) . ?
N3 C15 1.343(3) . ?
C3 C4 1.384(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.441(3) . ?
C7 C8 1.364(3) . ?
C7 C9 1.472(3) . ?
C8 C11 1.495(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9800 . ?
C13 C14 1.365(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.356(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
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
C8 N1 C1 C2 -178.3(2) . . . . ?
C12 N1 C1 C2 -8.3(4) . . . . ?
C8 N1 C1 C6 -0.8(2) . . . . ?
C12 N1 C1 C6 169.1(2) . . . . ?
N1 C1 C2 C3 177.8(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
N1 C1 C6 C7 1.5(2) . . . . ?
C5 C6 C7 C8 178.0(3) . . . . ?
C1 C6 C7 C8 -1.7(2) . . . . ?
C5 C6 C7 C9 -3.8(4) . . . . ?
C1 C6 C7 C9 176.6(2) . . . . ?
C6 C7 C8 N1 1.2(3) . . . . ?
C9 C7 C8 N1 -177.1(2) . . . . ?
C6 C7 C8 C11 175.5(2) . . . . ?
C9 C7 C8 C11 -2.8(4) . . . . ?
C1 N1 C8 C7 -0.3(3) . . . . ?
C12 N1 C8 C7 -169.7(2) . . . . ?
C1 N1 C8 C11 -174.7(2) . . . . ?
C12 N1 C8 C11 15.9(4) . . . . ?
C10 O2 C9 O1 0.3(4) . . . . ?
C10 O2 C9 C7 -179.4(2) . . . . ?
C8 C7 C9 O1 5.4(4) . . . . ?
C6 C7 C9 O1 -172.5(2) . . . . ?
C8 C7 C9 O2 -174.8(2) . . . . ?
C6 C7 C9 O2 7.2(3) . . . . ?
C7 C8 C11 F2 -146.3(2) . . . . ?
N1 C8 C11 F2 27.2(3) . . . . ?
C7 C8 C11 F1 94.9(3) . . . . ?
N1 C8 C11 F1 -91.6(3) . . . . ?
C15 N3 C12 N2 1.6(4) . . . . ?
C15 N3 C12 N1 178.7(2) . . . . ?
C13 N2 C12 N3 0.2(4) . . . . ?
C13 N2 C12 N1 -176.8(2) . . . . ?
C8 N1 C12 N3 37.9(3) . . . . ?
C1 N1 C12 N3 -130.0(2) . . . . ?
C8 N1 C12 N2 -144.8(2) . . . . ?
C1 N1 C12 N2 47.4(3) . . . . ?
C12 N2 C13 C14 -1.7(4) . . . . ?
N2 C13 C14 C15 1.2(4) . . . . ?
C12 N3 C15 C14 -2.2(3) . . . . ?
C13 C14 C15 N3 0.8(4) . . . . ?
