#------------------------------------------------------------------------------
#$Date: 2026-03-31 00:09:24 +0200 (Tue 31 de Mar de 2026) $
#$Revision: 305209 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/56/7135683.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_7135683
loop_
_publ_author_name
'Mondal, Sudeshna'
'Behura, Prabhudatta'
'Baidya, Mahiuddin'
_publ_section_title
;
 Free-amine-directed Ru(II)-catalyzed peri-selective C-H activation and
 annulation via ring-strain release
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D6CC01272H
_journal_year                    2026
_chemical_formula_sum            'C22 H19.54 N O'
_chemical_formula_weight         313.92
_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-2019/3
_audit_update_record
;
2026-01-07 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                97.870(2)
_cell_angle_beta                 91.598(2)
_cell_angle_gamma                111.305(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8979(4)
_cell_length_b                   9.6890(5)
_cell_length_c                   10.6306(5)
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.47
_cell_volume                     842.81(7)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            10106
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.941
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       Block
_exptl_crystal_F_000             333
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0523
_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)+(0.0749P)²+0.2290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2214
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc01272h2.cif
_cod_data_source_block           2054r
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7135683
_shelx_shelxl_version_number     2019/3
_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   0.976
_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
C1 C 0.2872(3) 0.7996(2) 0.4598(2) 0.0636(6) Uani 1 1 d . . . . .
C2 C 0.1541(3) 0.8449(3) 0.4466(3) 0.0755(7) Uani 1 1 d . . . . .
H2 H 0.075303 0.823710 0.504394 0.091 Uiso 1 1 calc R U . . .
C3 C 0.1406(3) 0.9188(3) 0.3505(3) 0.0744(7) Uani 1 1 d . . . . .
H3 H 0.055550 0.952433 0.344970 0.089 Uiso 1 1 calc R U . . .
C4 C 0.2530(2) 0.9448(2) 0.2601(2) 0.0606(6) Uani 1 1 d . . . . .
H4 H 0.239831 0.993061 0.193216 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3835(2) 0.90101(19) 0.26691(18) 0.0466(5) Uani 1 1 d . . . . .
C6 C 0.4080(2) 0.83033(19) 0.37080(18) 0.0490(5) Uani 1 1 d . . . . .
C7 C 0.5456(3) 0.7917(2) 0.39271(18) 0.0556(5) Uani 1 1 d . . . . .
C8 C 0.5540(3) 0.7201(3) 0.4935(2) 0.0794(7) Uani 1 1 d . . . . .
H8 H 0.642218 0.692186 0.506008 0.095 Uiso 1 1 calc R U . . .
C9 C 0.4329(4) 0.6878(4) 0.5783(3) 0.0993(10) Uani 1 1 d . . . . .
H9 H 0.441467 0.639363 0.646309 0.119 Uiso 1 1 calc R U . . .
C10 C 0.3038(4) 0.7268(3) 0.5616(2) 0.0900(9) Uani 1 1 d . . . . .
H10 H 0.224244 0.705051 0.618669 0.108 Uiso 1 1 calc R U . . .
C11 C 0.5701(2) 0.85919(19) 0.10184(18) 0.0454(4) Uani 1 1 d . . . . .
C12 C 0.6421(2) 0.7753(2) 0.17288(18) 0.0511(5) Uani 1 1 d D U . . .
C13 C 0.6852(2) 0.8343(2) 0.31190(19) 0.0585(5) Uani 1 1 d . . . . .
H13A H 0.765534 0.797957 0.342265 0.070 Uiso 1 1 calc R U . . .
H13B H 0.734478 0.942910 0.322826 0.070 Uiso 1 1 calc R U . . .
C17 C 0.9058(3) 0.4025(2) 0.1417(2) 0.0637(6) Uani 1 1 d . . . . .
C18 C 0.8695(3) 0.2510(3) 0.1023(2) 0.0702(6) Uani 1 1 d . . . . .
H18 H 0.776387 0.194936 0.048961 0.084 Uiso 1 1 calc R U . . .
C19 C 0.9694(4) 0.1824(3) 0.1412(3) 0.0804(7) Uani 1 1 d . . . . .
H19 H 0.944787 0.080963 0.112708 0.096 Uiso 1 1 calc R U . . .
C20 C 1.1044(3) 0.2625(3) 0.2215(3) 0.0811(8) Uani 1 1 d . . . . .
H20 H 1.171891 0.215802 0.247550 0.097 Uiso 1 1 calc R U . . .
C21 C 1.1400(3) 0.4099(3) 0.2632(3) 0.0787(7) Uani 1 1 d . . . . .
H21 H 1.231887 0.464367 0.318264 0.094 Uiso 1 1 calc R U . . .
C22 C 1.0415(3) 0.4794(3) 0.2247(2) 0.0730(7) Uani 1 1 d . . . . .
H22 H 1.066671 0.580491 0.255140 0.088 Uiso 1 1 calc R U . . .
N1 N 0.48270(18) 0.93190(16) 0.16444(15) 0.0486(4) Uani 1 1 d . . . . .
H1 H 0.488780 1.012722 0.136330 0.058 Uiso 1 1 calc R U . . .
O1 O 0.59616(18) 0.87376(15) -0.00991(13) 0.0602(4) Uani 1 1 d . . . . .
C14 C 0.6436(8) 0.6425(8) 0.1102(7) 0.0555(16) Uani 0.540(7) 1 d D U P A 1
H14A H 0.646373 0.645503 0.019472 0.067 Uiso 0.540(7) 1 calc R U P A 1
H14B H 0.546068 0.560515 0.123611 0.067 Uiso 0.540(7) 1 calc R U P A 1
C15 C 0.8090(7) 0.6141(6) 0.1661(4) 0.0645(15) Uani 0.540(7) 1 d D U P A 1
H15A H 0.907753 0.683009 0.139066 0.077 Uiso 0.540(7) 1 calc R U P A 1
H15B H 0.817117 0.624584 0.258410 0.077 Uiso 0.540(7) 1 calc R U P A 1
C16 C 0.7754(7) 0.4562(6) 0.1061(6) 0.0569(15) Uani 0.540(7) 1 d D U P A 1
H16A H 0.673576 0.391292 0.132119 0.068 Uiso 0.540(7) 1 calc R U P A 1
H16B H 0.764274 0.449240 0.014188 0.068 Uiso 0.540(7) 1 calc R U P A 1
C14' C 0.7084(9) 0.6883(8) 0.1088(7) 0.0462(15) Uani 0.460(7) 1 d D U P A 2
H14' H 0.760908 0.716297 0.036639 0.055 Uiso 0.460(7) 1 calc R U P A 2
C15' C 0.6983(8) 0.5291(7) 0.1568(5) 0.0573(17) Uani 0.460(7) 1 d D U P A 2
H15C H 0.723375 0.541059 0.247947 0.069 Uiso 0.460(7) 1 calc R U P A 2
H15D H 0.594625 0.448223 0.131177 0.069 Uiso 0.460(7) 1 calc R U P A 2
C16' C 0.8346(10) 0.5097(11) 0.0795(8) 0.073(2) Uani 0.460(7) 1 d D U P A 2
H16C H 0.919813 0.606654 0.079374 0.088 Uiso 0.460(7) 1 calc R U P A 2
H16D H 0.792825 0.466086 -0.007996 0.088 Uiso 0.460(7) 1 calc R U P A 2
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'
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
C10 C1 C2 120.5(2) . . ?
C10 C1 C6 119.3(2) . . ?
C2 C1 C6 120.2(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 N1 114.12(18) . . ?
C4 C5 C6 119.93(18) . . ?
N1 C5 C6 125.94(17) . . ?
C7 C6 C5 124.54(18) . . ?
C7 C6 C1 118.28(19) . . ?
C5 C6 C1 117.16(19) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 C13 119.0(2) . . ?
C6 C7 C13 121.52(18) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C1 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C1 C10 H10 119.4 . . ?
O1 C11 N1 119.30(16) . . ?
O1 C11 C12 121.87(17) . . ?
N1 C11 C12 118.64(17) . . ?
C14' C12 C11 118.6(4) . . ?
C14 C12 C11 117.4(3) . . ?
C14' C12 C13 122.5(4) . . ?
C14 C12 C13 126.5(3) . . ?
C11 C12 C13 115.52(16) . . ?
C7 C13 C12 114.61(17) . . ?
C7 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C7 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C22 C17 C18 117.5(2) . . ?
C22 C17 C16 127.2(3) . . ?
C18 C17 C16 114.3(3) . . ?
C22 C17 C16' 113.5(4) . . ?
C18 C17 C16' 127.4(4) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.3(2) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C11 N1 C5 132.71(15) . . ?
C11 N1 H1 113.6 . . ?
C5 N1 H1 113.6 . . ?
C12 C14 C15 109.4(5) . . ?
C12 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C12 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 101.9(5) . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15B 111.4 . . ?
C14 C15 H15B 111.4 . . ?
H15A C15 H15B 109.3 . . ?
C17 C16 C15 112.5(4) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C12 C14' C15' 120.2(5) . . ?
C12 C14' H14' 119.9 . . ?
C15' C14' H14' 119.9 . . ?
C16' C15' C14' 95.7(6) . . ?
C16' C15' H15C 112.6 . . ?
C14' C15' H15C 112.6 . . ?
C16' C15' H15D 112.6 . . ?
C14' C15' H15D 112.6 . . ?
H15C C15' H15D 110.1 . . ?
C15' C16' C17 109.4(5) . . ?
C15' C16' H16C 109.8 . . ?
C17 C16' H16C 109.8 . . ?
C15' C16' H16D 109.8 . . ?
C17 C16' H16D 109.8 . . ?
H16C C16' H16D 108.2 . . ?
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 C10 1.402(4) . ?
C1 C2 1.415(4) . ?
C1 C6 1.428(3) . ?
C2 C3 1.351(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.417(2) . ?
C5 C6 1.428(3) . ?
C6 C7 1.426(3) . ?
C7 C8 1.369(3) . ?
C7 C13 1.495(3) . ?
C8 C9 1.399(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.347(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.234(2) . ?
C11 N1 1.357(2) . ?
C11 C12 1.471(3) . ?
C12 C14' 1.322(8) . ?
C12 C14 1.370(7) . ?
C12 C13 1.495(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 C22 1.378(3) . ?
C17 C18 1.384(3) . ?
C17 C16 1.492(6) . ?
C17 C16' 1.599(8) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.351(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 H1 0.8600 . ?
C14 C15 1.699(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.492(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14' C15' 1.663(8) . ?
C14' H14' 0.9300 . ?
C15' C16' 1.536(8) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
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
C10 C1 C2 C3 178.1(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 3.1(3) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C3 C4 C5 N1 177.96(19) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C7 -174.66(17) . . . . ?
N1 C5 C6 C7 5.8(3) . . . . ?
C4 C5 C6 C1 4.0(3) . . . . ?
N1 C5 C6 C1 -175.58(16) . . . . ?
C10 C1 C6 C7 -2.9(3) . . . . ?
C2 C1 C6 C7 175.82(18) . . . . ?
C10 C1 C6 C5 178.38(19) . . . . ?
C2 C1 C6 C5 -2.9(3) . . . . ?
C5 C6 C7 C8 -178.08(19) . . . . ?
C1 C6 C7 C8 3.3(3) . . . . ?
C5 C6 C7 C13 5.0(3) . . . . ?
C1 C6 C7 C13 -173.62(17) . . . . ?
C6 C7 C8 C9 -2.0(4) . . . . ?
C13 C7 C8 C9 175.0(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C1 0.2(4) . . . . ?
C2 C1 C10 C9 -177.5(2) . . . . ?
C6 C1 C10 C9 1.2(4) . . . . ?
O1 C11 C12 C14' -14.0(4) . . . . ?
N1 C11 C12 C14' 171.1(4) . . . . ?
O1 C11 C12 C14 -42.6(4) . . . . ?
N1 C11 C12 C14 142.5(3) . . . . ?
O1 C11 C12 C13 145.58(19) . . . . ?
N1 C11 C12 C13 -29.3(3) . . . . ?
C8 C7 C13 C12 124.7(2) . . . . ?
C6 C7 C13 C12 -58.4(3) . . . . ?
C14' C12 C13 C7 -121.7(4) . . . . ?
C14 C12 C13 C7 -91.4(4) . . . . ?
C11 C12 C13 C7 79.6(2) . . . . ?
C22 C17 C18 C19 -2.5(4) . . . . ?
C16 C17 C18 C19 -172.2(4) . . . . ?
C16' C17 C18 C19 162.2(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C17 -1.0(4) . . . . ?
C18 C17 C22 C21 2.3(4) . . . . ?
C16 C17 C22 C21 170.5(4) . . . . ?
C16' C17 C22 C21 -164.5(3) . . . . ?
O1 C11 N1 C5 152.85(19) . . . . ?
C12 C11 N1 C5 -32.1(3) . . . . ?
C4 C5 N1 C11 -146.2(2) . . . . ?
C6 C5 N1 C11 33.4(3) . . . . ?
C11 C12 C14 C15 148.6(4) . . . . ?
C13 C12 C14 C15 -40.6(6) . . . . ?
C12 C14 C15 C16 170.3(4) . . . . ?
C22 C17 C16 C15 3.2(8) . . . . ?
C18 C17 C16 C15 171.7(4) . . . . ?
C14 C15 C16 C17 -179.7(4) . . . . ?
C11 C12 C14' C15' -145.8(5) . . . . ?
C13 C12 C14' C15' 56.1(7) . . . . ?
C12 C14' C15' C16' -162.7(6) . . . . ?
C14' C15' C16' C17 158.2(5) . . . . ?
C22 C17 C16' C15' -95.6(7) . . . . ?
C18 C17 C16' C15' 99.2(7) . . . . ?
