#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:50:44 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517521.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_4517521
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         'C25 H20 N2 O'
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43
_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             2019-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                110.430(3)
_cell_angle_beta                 100.373(3)
_cell_angle_gamma                101.270(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7963(9)
_cell_length_b                   10.3540(12)
_cell_length_c                   11.5419(14)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      29.616
_cell_measurement_theta_min      2.281
_cell_volume                     930.16(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      100.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17309
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.612
_diffrn_reflns_theta_min         2.452
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_correction_T_min  0.8426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1013 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.9490. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.191
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0410
_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)+(0.0458P)²+0.3945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4496
_reflns_number_total             5094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b05413_si_003.cif
_cod_data_source_block           0677_cg_0m
_cod_depositor_comments
;Adding full bibliography for 4517519--4517521.cif.

 Adding full bibliography for 4517519--4517521.cif.
;
_cod_original_cell_volume        930.16(18)
_cod_database_code               4517521
_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   0.985
_shelx_estimated_absorpt_t_min   0.973
_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:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in NVH 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 0.73078(10) 0.52426(9) 0.84701(8) 0.02237(17) Uani 1 1 d . . . . .
N1 N 0.74390(11) 0.47404(9) 0.64047(8) 0.01603(17) Uani 1 1 d . . . . .
N2 N 0.82716(12) 0.05977(10) 0.42947(9) 0.02112(19) Uani 1 1 d . . . . .
C1 C 0.74349(13) 0.56575(11) 0.76033(10) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.75926(13) 0.71548(11) 0.77528(10) 0.0174(2) Uani 1 1 d . . . . .
C3 C 0.76438(14) 0.81635(12) 0.89579(11) 0.0210(2) Uani 1 1 d . . . . .
H3 H 0.753627 0.786422 0.963625 0.025 Uiso 1 1 calc R . . . .
C4 C 0.78498(15) 0.95862(12) 0.91587(11) 0.0235(2) Uani 1 1 d . . . . .
H4 H 0.788908 1.026822 0.997543 0.028 Uiso 1 1 calc R . . . .
C5 C 0.80013(14) 1.00253(12) 0.81541(11) 0.0230(2) Uani 1 1 d . . . . .
H5 H 0.814840 1.100780 0.829719 0.028 Uiso 1 1 calc R . . . .
C6 C 0.79389(14) 0.90451(11) 0.69592(11) 0.0201(2) Uani 1 1 d . . . . .
H6 H 0.803575 0.935713 0.628657 0.024 Uiso 1 1 calc R . . . .
C7 C 0.77320(12) 0.75814(11) 0.67319(10) 0.01668(19) Uani 1 1 d . . . . .
C8 C 0.76944(13) 0.65276(11) 0.55167(10) 0.01697(19) Uani 1 1 d . . . . .
H8 H 0.777267 0.678821 0.481329 0.020 Uiso 1 1 calc R . . . .
C9 C 0.75450(12) 0.51522(11) 0.53905(9) 0.01529(19) Uani 1 1 d . . . . .
C10 C 0.75095(12) 0.38792(11) 0.42973(10) 0.01554(19) Uani 1 1 d . . . . .
C11 C 0.74587(12) 0.27688(11) 0.46663(10) 0.01564(19) Uani 1 1 d . . . . .
C12 C 0.73205(12) 0.12733(11) 0.38261(10) 0.01672(19) Uani 1 1 d . . . . .
C13 C 0.62305(13) 0.06108(11) 0.26039(10) 0.0207(2) Uani 1 1 d . . . . .
H13 H 0.554921 0.110506 0.231158 0.025 Uiso 1 1 calc R . . . .
C14 C 0.61615(15) -0.07773(12) 0.18275(11) 0.0252(2) Uani 1 1 d . . . . .
H14 H 0.543301 -0.125044 0.099393 0.030 Uiso 1 1 calc R . . . .
C15 C 0.71752(16) -0.14650(12) 0.22888(12) 0.0259(2) Uani 1 1 d . . . . .
H15 H 0.717529 -0.240742 0.177057 0.031 Uiso 1 1 calc R . . . .
C16 C 0.81864(15) -0.07443(12) 0.35223(12) 0.0243(2) Uani 1 1 d . . . . .
H16 H 0.885934 -0.122823 0.384057 0.029 Uiso 1 1 calc R . . . .
C17 C 0.74352(12) 0.32078(10) 0.60637(10) 0.01599(19) Uani 1 1 d . . . . .
C18 C 0.58850(13) 0.23339(12) 0.61678(11) 0.0211(2) Uani 1 1 d . . . . .
H18A H 0.584779 0.268219 0.706543 0.032 Uiso 1 1 calc GR . . . .
H18B H 0.586303 0.131877 0.586512 0.032 Uiso 1 1 calc GR . . . .
H18C H 0.495217 0.244144 0.563959 0.032 Uiso 1 1 calc GR . . . .
C19 C 0.89315(13) 0.31252(11) 0.69210(10) 0.0187(2) Uani 1 1 d . . . . .
H19A H 0.990213 0.364708 0.679576 0.028 Uiso 1 1 calc GR . . . .
H19B H 0.892177 0.211825 0.669234 0.028 Uiso 1 1 calc GR . . . .
H19C H 0.892670 0.355765 0.782258 0.028 Uiso 1 1 calc GR . . . .
C20 C 0.75242(12) 0.38917(10) 0.30232(9) 0.01570(19) Uani 1 1 d . . . . .
C21 C 0.85568(13) 0.32896(11) 0.23497(10) 0.0174(2) Uani 1 1 d . . . . .
H21 H 0.926810 0.286638 0.271509 0.021 Uiso 1 1 calc R . . . .
C22 C 0.85506(14) 0.33055(11) 0.11488(10) 0.0216(2) Uani 1 1 d . . . . .
H22 H 0.926809 0.290648 0.070462 0.026 Uiso 1 1 calc R . . . .
C23 C 0.74980(16) 0.39035(12) 0.05956(11) 0.0255(2) Uani 1 1 d . . . . .
H23 H 0.749187 0.391239 -0.022552 0.031 Uiso 1 1 calc R . . . .
C24 C 0.64568(15) 0.44870(12) 0.12536(11) 0.0253(2) Uani 1 1 d . . . . .
H24 H 0.572379 0.488224 0.087326 0.030 Uiso 1 1 calc R . . . .
C25 C 0.64772(14) 0.44979(11) 0.24624(10) 0.0203(2) Uani 1 1 d . . . . .
H25 H 0.577585 0.491974 0.291153 0.024 Uiso 1 1 calc R . . . .
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 C9 124.06(9) . . ?
C1 N1 C17 124.06(8) . . ?
C9 N1 C17 111.77(8) . . ?
C16 N2 C12 117.36(10) . . ?
O1 C1 N1 122.02(9) . . ?
O1 C1 C2 123.40(9) . . ?
N1 C1 C2 114.58(9) . . ?
C3 C2 C1 117.99(9) . . ?
C3 C2 C7 120.53(9) . . ?
C7 C2 C1 121.46(9) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.15(10) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.85(10) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.76(10) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.38(10) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 118.32(9) . . ?
C2 C7 C8 119.16(9) . . ?
C6 C7 C8 122.50(9) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.80(9) . . ?
C9 C8 H8 120.6 . . ?
N1 C9 C10 107.24(8) . . ?
C8 C9 N1 121.92(9) . . ?
C8 C9 C10 130.82(9) . . ?
C9 C10 C20 122.63(9) . . ?
C11 C10 C9 108.94(9) . . ?
C11 C10 C20 128.43(9) . . ?
C10 C11 C12 125.89(9) . . ?
C10 C11 C17 111.62(9) . . ?
C12 C11 C17 122.34(9) . . ?
N2 C12 C11 117.10(9) . . ?
N2 C12 C13 122.52(9) . . ?
C13 C12 C11 120.38(9) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.93(10) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.85(11) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.41(10) . . ?
C16 C15 H15 120.8 . . ?
N2 C16 C15 123.86(11) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
N1 C17 C11 100.31(8) . . ?
N1 C17 C18 110.87(8) . . ?
N1 C17 C19 109.89(8) . . ?
C11 C17 C18 110.49(9) . . ?
C11 C17 C19 113.37(8) . . ?
C18 C17 C19 111.42(9) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C10 121.26(9) . . ?
C21 C20 C25 118.79(9) . . ?
C25 C20 C10 119.95(9) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.51(10) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.28(10) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.43(10) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.58(10) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.40(10) . . ?
C24 C25 H25 119.8 . . ?
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 1.2327(13) . ?
N1 C1 1.3789(13) . ?
N1 C9 1.3903(13) . ?
N1 C17 1.4948(12) . ?
N2 C12 1.3460(13) . ?
N2 C16 1.3422(14) . ?
C1 C2 1.4741(14) . ?
C2 C3 1.4044(14) . ?
C2 C7 1.4116(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3780(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4032(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3816(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.4129(14) . ?
C7 C8 1.4351(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3572(14) . ?
C9 C10 1.4625(14) . ?
C10 C11 1.3541(14) . ?
C10 C20 1.4775(14) . ?
C11 C12 1.4793(14) . ?
C11 C17 1.5207(14) . ?
C12 C13 1.4000(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3855(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3883(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3849(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.5314(15) . ?
C17 C19 1.5339(14) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3983(14) . ?
C20 C25 1.3986(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.3909(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3912(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.3882(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.3882(16) . ?
C25 H25 0.9500 . ?
