#------------------------------------------------------------------------------
#$Date: 2022-04-03 22:17:19 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519375.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_4519375
loop_
_publ_author_name
'Khake, Shrikant M.'
'Chatani, Naoto'
_publ_section_title
;
 Rhodium(III)-Catalyzed Oxidative C--H Alkylation of Aniline Derivatives
 with Allylic Alcohols To Produce β-Aryl Ketones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              4394
_journal_page_last               4401
_journal_paper_doi               10.1021/acscatal.2c00854
_journal_year                    2022
_chemical_formula_moiety         'C15 H17 N3 O'
_chemical_formula_sum            'C15 H17 N3 O'
_chemical_formula_weight         255.32
_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
_cell_angle_alpha                95.9400
_cell_angle_beta                 109.1200
_cell_angle_gamma                110.3960
_cell_formula_units_Z            2
_cell_length_a                   7.6880
_cell_length_b                   9.1076
_cell_length_c                   10.6827
_cell_measurement_reflns_used    2096
_cell_measurement_temperature    123
_cell_measurement_theta_max      67.81
_cell_measurement_theta_min      6.08
_cell_volume                     642.108
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4736
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.160
_diffrn_reflns_theta_max         68.160
_diffrn_reflns_theta_min         5.346
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_correction_T_min  0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272.00
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0841
_refine_ls_shift/su_max          0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2251
_refine_ls_wR_factor_ref         0.2565
_reflns_number_gt                1938
_reflns_number_total             2272
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cs2c00854_si_002.cif
_cod_data_source_block           xcalibur
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 7550 2019-12-06 10:49:48Z antanas 

The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        642.1084
_cod_database_code               4519375
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1700(2) 0.20233(18) -0.30251(16) 0.0317(5) Uani 1 1 d . . .
N1 N 0.1968(3) 0.4803(2) 0.20622(19) 0.0248(5) Uani 1 1 d . . .
N2 N 0.3946(3) 0.3516(2) 0.16755(19) 0.0257(5) Uani 1 1 d . . .
N3 N 0.5007(3) 0.6390(2) 0.20116(19) 0.0279(5) Uani 1 1 d . . .
C1 C 0.0661(3) 0.3397(2) 0.2302(2) 0.0252(6) Uani 1 1 d . . .
C2 C -0.0687(3) 0.2053(3) 0.1207(2) 0.0245(6) Uani 1 1 d . . .
C3 C -0.1926(3) 0.0705(3) 0.1493(2) 0.0273(6) Uani 1 1 d . . .
C4 C -0.1854(3) 0.0724(3) 0.2817(2) 0.0277(6) Uani 1 1 d . . .
C5 C -0.0563(4) 0.2074(3) 0.3872(2) 0.0292(6) Uani 1 1 d . . .
C6 C 0.0725(3) 0.3437(3) 0.3631(2) 0.0260(6) Uani 1 1 d . . .
C7 C 0.2180(4) 0.4903(3) 0.4782(2) 0.0335(6) Uani 1 1 d . . .
C8 C 0.3709(3) 0.4897(2) 0.1912(2) 0.0235(6) Uani 1 1 d . . .
C9 C 0.5642(3) 0.3662(3) 0.1498(2) 0.0282(6) Uani 1 1 d . . .
C10 C 0.7064(3) 0.5121(3) 0.1551(2) 0.0287(6) Uani 1 1 d . . .
C11 C 0.6677(3) 0.6469(3) 0.1830(2) 0.0287(6) Uani 1 1 d . . .
C12 C -0.0796(4) 0.2105(3) -0.0224(2) 0.0284(6) Uani 1 1 d . . .
C13 C -0.2382(3) 0.0636(3) -0.1340(2) 0.0271(6) Uani 1 1 d . . .
C14 C -0.2460(3) 0.0741(3) -0.2762(2) 0.0267(6) Uani 1 1 d . . .
C15 C -0.3557(4) -0.0818(3) -0.3831(2) 0.0322(6) Uani 1 1 d . . .
H1 H -0.290(4) -0.029(3) 0.074(3) 0.038(7) Uiso 1 1 d . . .
H2 H -0.276(4) -0.024(3) 0.292(2) 0.023(6) Uiso 1 1 d . . .
H3 H -0.055(4) 0.210(4) 0.481(3) 0.045(8) Uiso 1 1 d . . .
H4 H 0.214(5) 0.487(4) 0.565(4) 0.060(10) Uiso 1 1 d . . .
H5 H 0.190(5) 0.582(4) 0.462(4) 0.057(9) Uiso 1 1 d . . .
H6 H 0.366(4) 0.518(3) 0.489(3) 0.037(7) Uiso 1 1 d . . .
H7 H 0.194(4) 0.571(4) 0.239(3) 0.041(7) Uiso 1 1 d . . .
H8 H 0.581(4) 0.265(3) 0.128(3) 0.031(6) Uiso 1 1 d . . .
H9 H 0.830(4) 0.518(3) 0.146(2) 0.026(6) Uiso 1 1 d . . .
H10 H 0.768(4) 0.753(3) 0.193(3) 0.032(6) Uiso 1 1 d . . .
H11 H -0.099(4) 0.312(4) -0.039(3) 0.040(7) Uiso 1 1 d . . .
H12 H 0.054(4) 0.228(3) -0.026(3) 0.037(7) Uiso 1 1 d . . .
H13 H -0.375(4) 0.047(3) -0.142(3) 0.034(7) Uiso 1 1 d . . .
H14 H -0.223(4) -0.036(4) -0.120(3) 0.038(7) Uiso 1 1 d . . .
H15 H -0.500(5) -0.133(4) -0.395(4) 0.059(9) Uiso 1 1 d . . .
H16 H -0.298(6) -0.158(4) -0.351(4) 0.064(10) Uiso 1 1 d . . .
H17 H -0.349(4) -0.073(3) -0.472(3) 0.042(8) 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
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)
;
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 122.44(17) . . ?
C8 N1 H7 116.9(19) . . ?
C1 N1 H7 114.7(19) . . ?
C9 N2 C8 115.65(18) . . ?
C11 N3 C8 115.33(18) . . ?
C6 C1 C2 121.86(19) . . ?
C6 C1 N1 118.29(19) . . ?
C2 C1 N1 119.80(18) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 C12 122.3(2) . . ?
C1 C2 C12 119.99(18) . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H1 118.7(16) . . ?
C2 C3 H1 120.4(16) . . ?
C5 C4 C3 120.58(19) . . ?
C5 C4 H2 124.2(14) . . ?
C3 C4 H2 115.2(14) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H3 120.5(17) . . ?
C6 C5 H3 119.3(17) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 120.74(19) . . ?
C1 C6 C7 120.57(19) . . ?
C6 C7 H4 117(2) . . ?
C6 C7 H5 111(2) . . ?
H4 C7 H5 102(3) . . ?
C6 C7 H6 111.7(15) . . ?
H4 C7 H6 107(3) . . ?
H5 C7 H6 107(3) . . ?
N2 C8 N3 126.65(19) . . ?
N2 C8 N1 117.76(18) . . ?
N3 C8 N1 115.59(18) . . ?
N2 C9 C10 122.9(2) . . ?
N2 C9 H8 116.6(14) . . ?
C10 C9 H8 120.4(14) . . ?
C9 C10 C11 116.3(2) . . ?
C9 C10 H9 120.4(15) . . ?
C11 C10 H9 123.1(15) . . ?
N3 C11 C10 123.1(2) . . ?
N3 C11 H10 118.2(16) . . ?
C10 C11 H10 118.7(16) . . ?
C13 C12 C2 115.82(18) . . ?
C13 C12 H11 111.7(16) . . ?
C2 C12 H11 106.1(17) . . ?
C13 C12 H12 108.6(16) . . ?
C2 C12 H12 109.4(16) . . ?
H11 C12 H12 105(2) . . ?
C12 C13 C14 114.27(18) . . ?
C12 C13 H13 112.0(15) . . ?
C14 C13 H13 102.9(16) . . ?
C12 C13 H14 113.2(16) . . ?
C14 C13 H14 106.9(17) . . ?
H13 C13 H14 107(2) . . ?
O1 C14 C15 121.9(2) . . ?
O1 C14 C13 122.07(19) . . ?
C15 C14 C13 116.03(18) . . ?
C14 C15 H15 111(2) . . ?
C14 C15 H16 108(2) . . ?
H15 C15 H16 105(3) . . ?
C14 C15 H17 114.4(17) . . ?
H15 C15 H17 109(3) . . ?
H16 C15 H17 108(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
O1 C14 1.218(3) . ?
N1 C8 1.374(3) . ?
N1 C1 1.433(3) . ?
N1 H7 0.88(3) . ?
N2 C9 1.342(3) . ?
N2 C8 1.342(3) . ?
N3 C11 1.338(3) . ?
N3 C8 1.346(3) . ?
C1 C6 1.401(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.400(3) . ?
C2 C12 1.510(3) . ?
C3 C4 1.395(3) . ?
C3 H1 1.00(3) . ?
C4 C5 1.377(3) . ?
C4 H2 0.95(3) . ?
C5 C6 1.401(3) . ?
C5 H3 1.00(3) . ?
C6 C7 1.504(3) . ?
C7 H4 0.94(4) . ?
C7 H5 0.95(4) . ?
C7 H6 1.04(3) . ?
C9 C10 1.377(3) . ?
C9 H8 0.99(3) . ?
C10 C11 1.386(3) . ?
C10 H9 0.97(3) . ?
C11 H10 0.97(3) . ?
C12 C13 1.510(3) . ?
C12 H11 1.01(3) . ?
C12 H12 1.00(3) . ?
C13 C14 1.516(3) . ?
C13 H13 0.99(3) . ?
C13 H14 0.98(3) . ?
C14 C15 1.493(3) . ?
C15 H15 1.00(4) . ?
C15 H16 0.98(4) . ?
C15 H17 0.98(3) . ?
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
N1 H7 O1 . . 2_565 3.065(3) 0.88(4) 2.19(4) 175(3) 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
C8 N1 C1 C6 102.9(2) . . . . ?
C8 N1 C1 C2 -79.4(3) . . . . ?
C6 C1 C2 C3 -2.8(3) . . . . ?
N1 C1 C2 C3 179.70(16) . . . . ?
C6 C1 C2 C12 176.02(17) . . . . ?
N1 C1 C2 C12 -1.5(3) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C12 C2 C3 C4 -176.94(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
N1 C1 C6 C5 179.33(17) . . . . ?
C2 C1 C6 C7 -179.57(18) . . . . ?
N1 C1 C6 C7 -2.0(3) . . . . ?
C9 N2 C8 N3 -1.4(3) . . . . ?
C9 N2 C8 N1 178.22(16) . . . . ?
C11 N3 C8 N2 1.2(3) . . . . ?
C11 N3 C8 N1 -178.38(16) . . . . ?
C1 N1 C8 N2 15.2(3) . . . . ?
C1 N1 C8 N3 -165.14(19) . . . . ?
C8 N2 C9 C10 0.0(3) . . . . ?
N2 C9 C10 C11 1.3(3) . . . . ?
C8 N3 C11 C10 0.3(3) . . . . ?
C9 C10 C11 N3 -1.5(3) . . . . ?
C3 C2 C12 C13 2.2(3) . . . . ?
C1 C2 C12 C13 -176.49(18) . . . . ?
C2 C12 C13 C14 179.37(16) . . . . ?
C12 C13 C14 O1 -17.9(3) . . . . ?
C12 C13 C14 C15 163.2(2) . . . . ?
