#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:50:44 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517520.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_4517520
loop_
_publ_author_name
'Zhu, Cuiju'
'Kuniyil, Rositha'
'Jei, Becky B.'
'Ackermann, Lutz'
_publ_section_title
;
 Domino C--H Activation/Directing Group Migration/Alkyne Annulation:
 Unique Selectivity by d6-Cobalt(III) Catalysts
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4444
_journal_page_last               4450
_journal_paper_doi               10.1021/acscatal.9b05413
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_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     dual
_audit_creation_date             2019-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                105.947(4)
_cell_angle_beta                 96.819(4)
_cell_angle_gamma                97.151(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0581(12)
_cell_length_b                   9.9273(12)
_cell_length_c                   10.2645(12)
_cell_measurement_reflns_used    1492
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.85
_cell_volume                     869.20(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24237
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.756
_diffrn_reflns_theta_min         2.296
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_correction_T_min  0.8417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0919 before and 0.0406 after correction. The Ratio of minimum to maximum transmission is 0.9480. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0409
_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)+(0.0508P)²+0.3749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4180
_reflns_number_total             4505
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b05413_si_004.cif
_cod_data_source_block           0577_cg_0m
_cod_depositor_comments
;Adding full bibliography for 4517519--4517521.cif.

 Adding full bibliography for 4517519--4517521.cif.
;
_cod_database_code               4517520
_shelx_shelxl_version_number     2018/3
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.09886(9) 0.07333(8) 0.28063(8) 0.02278(17) Uani 1 1 d . . . . .
N1 N 0.18804(9) 0.31175(9) 0.37286(8) 0.01666(17) Uani 1 1 d . . . . .
N2 N 0.35230(10) 0.54793(10) 0.09888(9) 0.02066(18) Uani 1 1 d . . . . .
C1 C 0.14021(11) 0.17688(11) 0.38370(10) 0.01834(19) Uani 1 1 d . . . . .
C2 C 0.14293(11) 0.17200(11) 0.52323(11) 0.0196(2) Uani 1 1 d . . . . .
H2 H 0.114633 0.082701 0.538170 0.023 Uiso 1 1 calc R . . . .
C3 C 0.18417(11) 0.28938(11) 0.63488(10) 0.0189(2) Uani 1 1 d . . . . .
C4 C 0.22863(11) 0.42398(11) 0.61501(10) 0.01846(19) Uani 1 1 d . . . . .
H4 H 0.257196 0.507129 0.691064 0.022 Uiso 1 1 calc R . . . .
C5 C 0.22923(11) 0.43074(10) 0.48433(10) 0.01663(19) Uani 1 1 d . . . . .
C6 C 0.27069(11) 0.55165(10) 0.43343(10) 0.01681(19) Uani 1 1 d . . . . .
C7 C 0.25789(11) 0.50522(10) 0.29569(10) 0.01694(19) Uani 1 1 d . . . . .
C8 C 0.27773(11) 0.59493(10) 0.20358(10) 0.01705(19) Uani 1 1 d . . . . .
C9 C 0.21806(11) 0.72116(11) 0.22424(10) 0.0196(2) Uani 1 1 d . . . . .
H9 H 0.165405 0.751545 0.298975 0.023 Uiso 1 1 calc R . . . .
C10 C 0.23670(12) 0.80118(11) 0.13451(11) 0.0217(2) Uani 1 1 d . . . . .
H10 H 0.196230 0.886742 0.145988 0.026 Uiso 1 1 calc R . . . .
C11 C 0.31568(12) 0.75408(11) 0.02734(11) 0.0217(2) Uani 1 1 d . . . . .
H11 H 0.331533 0.807219 -0.035338 0.026 Uiso 1 1 calc R . . . .
C12 C 0.37076(12) 0.62786(12) 0.01403(11) 0.0216(2) Uani 1 1 d . . . . .
H12 H 0.424731 0.596042 -0.059433 0.026 Uiso 1 1 calc R . . . .
C13 C 0.20473(11) 0.34543(10) 0.24166(10) 0.01721(19) Uani 1 1 d . . . . .
C14 C 0.32023(12) 0.26349(11) 0.17104(11) 0.0214(2) Uani 1 1 d . . . . .
H14A H 0.417993 0.290965 0.231542 0.032 Uiso 1 1 calc GR . . . .
H14B H 0.330353 0.285833 0.084950 0.032 Uiso 1 1 calc GR . . . .
H14C H 0.286194 0.161279 0.151485 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.05225(12) 0.31252(12) 0.14720(11) 0.0230(2) Uani 1 1 d . . . . .
H15A H 0.014388 0.210338 0.120841 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.064632 0.341490 0.064717 0.035 Uiso 1 1 calc GR . . . .
H15C H -0.019732 0.364697 0.195657 0.035 Uiso 1 1 calc GR . . . .
C16 C 0.31822(11) 0.69761(10) 0.52643(10) 0.01684(19) Uani 1 1 d . . . . .
C17 C 0.45621(11) 0.77712(11) 0.52529(10) 0.0191(2) Uani 1 1 d . . . . .
H17 H 0.520711 0.737596 0.463772 0.023 Uiso 1 1 calc R . . . .
C18 C 0.49941(12) 0.91393(11) 0.61391(11) 0.0222(2) Uani 1 1 d . . . . .
H18 H 0.593926 0.967271 0.613527 0.027 Uiso 1 1 calc R . . . .
C19 C 0.40514(13) 0.97303(11) 0.70299(11) 0.0235(2) Uani 1 1 d . . . . .
H19 H 0.434947 1.066796 0.763134 0.028 Uiso 1 1 calc R . . . .
C20 C 0.26694(13) 0.89495(11) 0.70422(11) 0.0228(2) Uani 1 1 d . . . . .
H20 H 0.201900 0.935500 0.764655 0.027 Uiso 1 1 calc R . . . .
C21 C 0.22434(12) 0.75748(11) 0.61677(11) 0.0200(2) Uani 1 1 d . . . . .
H21 H 0.130521 0.703809 0.618501 0.024 Uiso 1 1 calc R . . . .
C22 C 0.18549(14) 0.27928(12) 0.77841(11) 0.0254(2) Uani 1 1 d . . . . .
H22A H 0.135584 0.184652 0.774968 0.038 Uiso 1 1 calc GR . . . .
H22B H 0.131852 0.351333 0.829097 0.038 Uiso 1 1 calc GR . . . .
H22C H 0.289904 0.295281 0.824781 0.038 Uiso 1 1 calc GR . . . .
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
C1 N1 C13 125.09(8) . . ?
C5 N1 C1 123.29(9) . . ?
C5 N1 C13 111.60(8) . . ?
C12 N2 C8 117.65(9) . . ?
O1 C1 N1 121.33(9) . . ?
O1 C1 C2 124.71(9) . . ?
N1 C1 C2 113.95(9) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 C1 123.28(9) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 C4 119.32(9) . . ?
C2 C3 C22 121.47(9) . . ?
C4 C3 C22 119.20(9) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.40(9) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C6 107.79(8) . . ?
C4 C5 N1 121.72(9) . . ?
C4 C5 C6 130.49(9) . . ?
C5 C6 C16 122.11(9) . . ?
C7 C6 C5 108.88(9) . . ?
C7 C6 C16 129.01(9) . . ?
C6 C7 C8 126.08(9) . . ?
C6 C7 C13 111.32(9) . . ?
C8 C7 C13 122.38(8) . . ?
N2 C8 C7 116.91(9) . . ?
N2 C8 C9 122.27(9) . . ?
C9 C8 C7 120.81(9) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.18(9) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.74(10) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.41(10) . . ?
C12 C11 H11 120.8 . . ?
N2 C12 C11 123.75(10) . . ?
N2 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
N1 C13 C7 100.37(7) . . ?
N1 C13 C14 109.92(8) . . ?
N1 C13 C15 110.88(8) . . ?
C7 C13 C14 113.59(8) . . ?
C7 C13 C15 110.30(8) . . ?
C14 C13 C15 111.31(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C6 120.90(9) . . ?
C21 C16 C6 119.84(9) . . ?
C21 C16 C17 119.25(9) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.13(9) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.30(10) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.98(10) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.79(10) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.55(10) . . ?
C20 C21 H21 119.7 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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 C1 1.2364(12) . ?
N1 C1 1.3934(13) . ?
N1 C5 1.3747(12) . ?
N1 C13 1.4938(12) . ?
N2 C8 1.3432(13) . ?
N2 C12 1.3407(13) . ?
C1 C2 1.4437(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3664(14) . ?
C3 C4 1.4228(14) . ?
C3 C22 1.5027(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3620(14) . ?
C5 C6 1.4607(13) . ?
C6 C7 1.3470(14) . ?
C6 C16 1.4776(13) . ?
C7 C8 1.4773(13) . ?
C7 C13 1.5227(14) . ?
C8 C9 1.3990(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3833(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3886(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3839(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.5329(14) . ?
C13 C15 1.5330(14) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3959(14) . ?
C16 C21 1.3951(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.3890(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.3874(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3913(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3895(14) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
