#------------------------------------------------------------------------------
#$Date: 2021-10-06 16:54:20 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128920.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_7128920
loop_
_publ_author_name
'Sawano, Takahiro'
'Matsui, Takeshi'
'Koga, Marina'
'Ishikawa, Eri'
'Takeuchi, Ryo'
_publ_section_title
;
 Iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with
 secondary allylic alcohols.
;
_journal_issue                   76
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9684
_journal_page_last               9687
_journal_paper_doi               10.1039/d1cc03968g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C12 H10 F6 N2 O4'
_chemical_formula_sum            'C12 H10 F6 N2 O4'
_chemical_formula_weight         360.21
_chemical_melting_point          328
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-04-26 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                115.47(2)
_cell_angle_beta                 98.08(2)
_cell_angle_gamma                92.02(3)
_cell_formula_units_Z            2
_cell_length_a                   7.449(5)
_cell_length_b                   10.164(8)
_cell_length_c                   11.085(6)
_cell_measurement_reflns_used    4179
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.17
_cell_volume                     745.9(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7411
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_min         3.163
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364.00
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1140P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.2212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1618
_reflns_number_total             3387
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1cc03968g2.cif
_cod_data_source_block           SawaTM347B
_cod_depositor_comments
'Adding full bibliography for 7128920--7128921.cif.'
_cod_original_cell_volume        745.9(8)
_cod_database_code               7128920
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
F1 F 0.7482(4) 0.8771(3) 0.4856(3) 0.1334(11) Uani 1 1 d . . . . .
F2 F 1.0129(4) 0.8273(3) 0.4743(3) 0.1212(10) Uani 1 1 d . . . . .
F3 F 0.9328(5) 0.9341(3) 0.6647(2) 0.1273(11) Uani 1 1 d . . . . .
F4 F 0.6729(5) 0.0112(3) 0.1647(4) 0.1481(13) Uani 1 1 d . . . . .
F5 F 0.5643(5) 0.0798(3) 0.3433(3) 0.1412(13) Uani 1 1 d . . . . .
F6 F 0.4012(4) 0.0434(3) 0.1588(3) 0.1311(11) Uani 1 1 d . . . . .
O1 O 0.7861(6) 0.5855(3) 0.4207(2) 0.1414(16) Uani 1 1 d . . . . .
O2 O 0.8293(5) 0.6748(3) 0.6419(2) 0.1075(11) Uani 1 1 d . . . . .
O3 O 0.6811(5) 0.3352(3) 0.3800(2) 0.1088(12) Uani 1 1 d . . . . .
O4 O 0.5787(6) 0.2873(4) 0.1682(3) 0.1248(13) Uani 1 1 d . . . . .
N1 N 0.8724(3) 0.6931(3) 0.9960(2) 0.0571(7) Uani 1 1 d . . . . .
N2 N 0.7682(4) 0.5037(3) 0.7692(2) 0.0575(7) Uani 1 1 d . . . . .
C1 C 0.8670(5) 0.7001(4) 1.1244(3) 0.0631(9) Uani 1 1 d . . . . .
C2 C 0.7886(4) 0.5748(4) 1.1137(3) 0.0620(9) Uani 1 1 d . . . . .
C3 C 0.7383(4) 0.4787(3) 0.9713(3) 0.0531(7) Uani 1 1 d . . . . .
C4 C 0.6548(5) 0.3383(4) 0.8933(3) 0.0659(9) Uani 1 1 d . . . . .
C5 C 0.6335(5) 0.2831(5) 0.7531(4) 0.0711(9) Uani 1 1 d . . . . .
C6 C 0.6880(5) 0.3662(4) 0.6938(3) 0.0679(9) Uani 1 1 d . . . . .
C7 C 0.7955(4) 0.5599(3) 0.9051(3) 0.0490(7) Uani 1 1 d . . . . .
C8 C 0.9555(7) 0.8070(5) 0.9699(5) 0.0808(12) Uani 1 1 d . . . . .
C9 C 0.8257(5) 0.6825(4) 0.5364(3) 0.0663(9) Uani 1 1 d . . . . .
C10 C 0.8822(6) 0.8314(4) 0.5430(3) 0.0714(9) Uani 1 1 d . . . . .
C11 C 0.6107(5) 0.2536(4) 0.2582(3) 0.0681(9) Uani 1 1 d . . . . .
C12 C 0.5618(6) 0.0975(4) 0.2330(4) 0.0750(10) Uani 1 1 d . . . . .
H1 H 0.909(4) 0.779(4) 1.205(4) 0.067(9) Uiso 1 1 d . . . . .
H2 H 0.776(4) 0.549(4) 1.186(3) 0.063(9) Uiso 1 1 d . . . . .
H3 H 0.618(4) 0.283(4) 0.935(3) 0.068(9) Uiso 1 1 d . . . . .
H4 H 0.577(5) 0.195(5) 0.698(4) 0.080(12) Uiso 1 1 d . . . . .
H5 H 0.676(4) 0.332(4) 0.598(3) 0.070(9) Uiso 1 1 d . . . . .
H6 H 0.785(4) 0.551(3) 0.731(3) 0.046(8) Uiso 1 1 d . . . . .
H7 H 1.054(7) 0.777(6) 0.924(5) 0.126(18) Uiso 1 1 d . . . . .
H8 H 0.896(8) 0.833(6) 0.903(6) 0.15(2) Uiso 1 1 d . . . . .
H9 H 0.999(7) 0.889(7) 1.046(6) 0.136(19) Uiso 1 1 d . . . . .
H10 H 0.722(7) 0.430(7) 0.389(5) 0.137(18) 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C11 O3 H10 110(3) . . ?
C7 N1 C1 106.8(3) . . ?
C7 N1 C8 127.6(3) . . ?
C1 N1 C8 125.6(3) . . ?
C7 N2 C6 119.7(3) . . ?
C7 N2 H6 122(2) . . ?
C6 N2 H6 117(2) . . ?
C2 C1 N1 110.8(3) . . ?
C2 C1 H1 123(2) . . ?
N1 C1 H1 126(2) . . ?
C1 C2 C3 107.1(3) . . ?
C1 C2 H2 127(2) . . ?
C3 C2 H2 126(2) . . ?
C4 C3 C7 118.5(3) . . ?
C4 C3 C2 136.5(3) . . ?
C7 C3 C2 105.1(3) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H3 120(2) . . ?
C5 C4 H3 122(2) . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H4 117(2) . . ?
C4 C5 H4 122(2) . . ?
N2 C6 C5 120.9(3) . . ?
N2 C6 H5 115(2) . . ?
C5 C6 H5 124(2) . . ?
N1 C7 N2 128.3(3) . . ?
N1 C7 C3 110.3(2) . . ?
N2 C7 C3 121.4(3) . . ?
N1 C8 H7 112(3) . . ?
N1 C8 H8 121(4) . . ?
H7 C8 H8 92(4) . . ?
N1 C8 H9 113(3) . . ?
H7 C8 H9 106(5) . . ?
H8 C8 H9 110(5) . . ?
O2 C9 O1 129.1(3) . . ?
O2 C9 C10 117.6(3) . . ?
O1 C9 C10 113.3(3) . . ?
F3 C10 F2 107.8(3) . . ?
F3 C10 F1 106.4(3) . . ?
F2 C10 F1 103.5(3) . . ?
F3 C10 C9 114.2(3) . . ?
F2 C10 C9 112.8(3) . . ?
F1 C10 C9 111.4(3) . . ?
O4 C11 O3 127.5(4) . . ?
O4 C11 C12 119.8(3) . . ?
O3 C11 C12 112.7(3) . . ?
F4 C12 F6 104.6(4) . . ?
F4 C12 F5 106.6(4) . . ?
F6 C12 F5 107.2(3) . . ?
F4 C12 C11 111.2(3) . . ?
F6 C12 C11 112.4(3) . . ?
F5 C12 C11 114.3(3) . . ?
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 1.314(4) . ?
F2 C10 1.309(4) . ?
F3 C10 1.292(4) . ?
F4 C12 1.298(5) . ?
F5 C12 1.308(4) . ?
F6 C12 1.303(4) . ?
O1 C9 1.221(4) . ?
O2 C9 1.202(3) . ?
O3 C11 1.262(4) . ?
O3 H10 0.96(6) . ?
O4 C11 1.185(4) . ?
N1 C7 1.337(4) . ?
N1 C1 1.400(4) . ?
N1 C8 1.448(5) . ?
N2 C7 1.343(4) . ?
N2 C6 1.343(5) . ?
N2 H6 0.78(3) . ?
C1 C2 1.333(5) . ?
C1 H1 0.91(4) . ?
C2 C3 1.439(4) . ?
C2 H2 0.95(3) . ?
C3 C4 1.376(5) . ?
C3 C7 1.409(4) . ?
C4 C5 1.389(5) . ?
C4 H3 0.93(4) . ?
C5 C6 1.357(5) . ?
C5 H4 0.88(4) . ?
C6 H5 0.96(3) . ?
C8 H7 0.94(5) . ?
C8 H8 0.95(6) . ?
C8 H9 0.90(6) . ?
C9 C10 1.524(5) . ?
C11 C12 1.508(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H10 O1 . . . 2.459(5) 0.99(7) 1.48(6) 170(5) no
N2 H6 O2 . . . 2.731(5) 0.80(4) 1.93(4) 178(2) no
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
C7 N1 C1 C2 -0.1(4) . . . . ?
C8 N1 C1 C2 -176.9(4) . . . . ?
N1 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 -179.7(4) . . . . ?
C1 C2 C3 C7 0.3(3) . . . . ?
C7 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 -2.1(5) . . . . ?
C7 N2 C6 C5 0.2(5) . . . . ?
C4 C5 C6 N2 1.5(6) . . . . ?
C1 N1 C7 N2 179.1(3) . . . . ?
C8 N1 C7 N2 -4.1(5) . . . . ?
C1 N1 C7 C3 0.3(3) . . . . ?
C8 N1 C7 C3 177.1(4) . . . . ?
C6 N2 C7 N1 180.0(3) . . . . ?
C6 N2 C7 C3 -1.3(4) . . . . ?
C4 C3 C7 N1 179.7(3) . . . . ?
C2 C3 C7 N1 -0.4(3) . . . . ?
C4 C3 C7 N2 0.7(4) . . . . ?
C2 C3 C7 N2 -179.3(3) . . . . ?
O2 C9 C10 F3 1.5(5) . . . . ?
O1 C9 C10 F3 -176.9(4) . . . . ?
O2 C9 C10 F2 125.1(4) . . . . ?
O1 C9 C10 F2 -53.4(5) . . . . ?
O2 C9 C10 F1 -119.0(4) . . . . ?
O1 C9 C10 F1 62.5(5) . . . . ?
O4 C11 C12 F4 74.0(5) . . . . ?
O3 C11 C12 F4 -107.2(4) . . . . ?
O4 C11 C12 F6 -42.8(5) . . . . ?
O3 C11 C12 F6 135.9(4) . . . . ?
O4 C11 C12 F5 -165.3(4) . . . . ?
O3 C11 C12 F5 13.5(5) . . . . ?
