#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:02:09 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290875 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/11/1571192.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_1571192
loop_
_publ_author_name
'Höeg, Finn'
'Luxenberger, Lea'
'Fedulin, Andrey'
'Jacobi von Wangelin, Axel'
_publ_section_title
;
 Cobalt-catalyzed double hydroboration of pyridines
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              5201
_journal_page_last               5210
_journal_paper_doi               10.1039/D3SC05418G
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H19 N O2'
_chemical_formula_sum            'C15 H19 N O2'
_chemical_formula_weight         245.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-10 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.501(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1533(4)
_cell_length_b                   6.0972(2)
_cell_length_c                   15.4812(4)
_cell_measurement_reflns_used    7547
_cell_measurement_temperature    99.95(13)
_cell_measurement_theta_max      76.0020
_cell_measurement_theta_min      6.3300
_cell_volume                     1313.58(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.95(13)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13446
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.510
_diffrn_reflns_theta_min         2.903
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0627
_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)+(0.1276P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2536
_reflns_number_total             2734
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05418g2.cif
_cod_data_source_block           FH74
_cod_depositor_comments
'Adding full bibliography for 1571191--1571195.cif.'
_cod_database_code               1571192
_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.
;
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
1.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.5578(2) 0.6111(5) 0.33625(18) 0.0371(6) Uani 1 1 d . . . . .
H1A H 0.581950 0.747211 0.367578 0.044 Uiso 1 1 calc R U . . .
H1B H 0.487829 0.627768 0.314982 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6088(2) 0.5748(5) 0.25791(18) 0.0356(6) Uani 1 1 d . . . . .
H2 H 0.590227 0.697327 0.215236 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5725(2) 0.3634(5) 0.21327(18) 0.0357(6) Uani 1 1 d . . . . .
C4 C 0.5435(2) 0.2026(5) 0.26076(19) 0.0387(6) Uani 1 1 d . . . . .
H4 H 0.517501 0.074499 0.230476 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5487(3) 0.2092(5) 0.3583(2) 0.0433(7) Uani 1 1 d . . . . .
H5A H 0.485436 0.167459 0.371877 0.052 Uiso 1 1 calc R U . . .
H5B H 0.596410 0.099771 0.386183 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7182(2) 0.5830(5) 0.28871(17) 0.0367(6) Uani 1 1 d . . . . .
H6 H 0.736326 0.476583 0.338101 0.044 Uiso 1 1 calc R U . . .
C7 C 0.7723(2) 0.5232(5) 0.21533(17) 0.0355(6) Uani 1 1 d . . . . .
C8 C 0.8090(2) 0.3150(5) 0.20991(18) 0.0388(6) Uani 1 1 d . . . . .
H8 H 0.803689 0.209934 0.254115 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8540(2) 0.2573(6) 0.1395(2) 0.0420(7) Uani 1 1 d . . . . .
H9 H 0.879274 0.113817 0.136065 0.050 Uiso 1 1 calc R U . . .
C10 C 0.8614(2) 0.4102(7) 0.0751(2) 0.0453(7) Uani 1 1 d . . . . .
H10 H 0.891824 0.371746 0.027314 0.054 Uiso 1 1 calc R U . . .
C11 C 0.8246(2) 0.6190(6) 0.0800(2) 0.0453(7) Uani 1 1 d . . . . .
H11 H 0.829341 0.723315 0.035399 0.054 Uiso 1 1 calc R U . . .
C12 C 0.7805(2) 0.6770(5) 0.1506(2) 0.0408(6) Uani 1 1 d . . . . .
H12 H 0.756160 0.821165 0.154317 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5656(2) 0.3452(6) 0.11516(18) 0.0431(7) Uani 1 1 d . . . . .
H13A H 0.538042 0.202577 0.095118 0.065 Uiso 1 1 calc R U . . .
H13B H 0.629881 0.358550 0.100565 0.065 Uiso 1 1 calc R U . . .
H13C H 0.524362 0.462611 0.086039 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6141(2) 0.4378(5) 0.48192(18) 0.0367(6) Uani 1 1 d . . . . .
C15 C 0.6427(2) 0.6602(6) 0.52117(19) 0.0442(7) Uani 1 1 d . . . . .
H15A H 0.665220 0.645221 0.584607 0.066 Uiso 1 1 calc R U . . .
H15B H 0.587099 0.758749 0.510311 0.066 Uiso 1 1 calc R U . . .
H15C H 0.694375 0.721052 0.494034 0.066 Uiso 1 1 calc R U . . .
N1 N 0.57557(18) 0.4250(4) 0.39597(15) 0.0363(5) Uani 1 1 d . . . . .
O1 O 0.74157(17) 0.7986(4) 0.32093(14) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.62698(16) 0.2710(4) 0.52766(13) 0.0432(5) Uani 1 1 d . . . . .
H1O H 0.788(4) 0.810(8) 0.366(4) 0.055(12) 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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C2 109.7(2) . . ?
C1 C2 H2 108.0 . . ?
C3 C2 C1 108.4(2) . . ?
C3 C2 H2 108.0 . . ?
C3 C2 C6 114.2(2) . . ?
C6 C2 C1 110.0(2) . . ?
C6 C2 H2 108.0 . . ?
C2 C3 C13 118.6(3) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 C13 122.0(3) . . ?
C3 C4 H4 117.6 . . ?
C3 C4 C5 124.9(3) . . ?
C5 C4 H4 117.6 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N1 C5 C4 112.8(2) . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C2 C6 H6 108.7 . . ?
C7 C6 C2 112.1(2) . . ?
C7 C6 H6 108.7 . . ?
O1 C6 C2 107.2(2) . . ?
O1 C6 H6 108.7 . . ?
O1 C6 C7 111.4(2) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 C12 119.6(3) . . ?
C12 C7 C6 119.6(3) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.0(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 118.7(3) . . ?
O2 C14 C15 120.6(2) . . ?
O2 C14 N1 120.7(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C5 116.5(2) . . ?
C14 N1 C1 125.1(3) . . ?
C14 N1 C5 118.4(3) . . ?
C6 O1 H1O 117(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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.536(3) . ?
C1 N1 1.456(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.508(4) . ?
C2 C6 1.536(4) . ?
C3 C4 1.335(4) . ?
C3 C13 1.508(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.499(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N1 1.461(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.526(4) . ?
C6 O1 1.423(3) . ?
C7 C8 1.380(4) . ?
C7 C12 1.393(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.405(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.511(5) . ?
C14 N1 1.345(4) . ?
C14 O2 1.233(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 H1O 0.87(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O2 0.87(6) 1.87(6) 2.719(3) 166(5) 4_656 yes
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
C1 C2 C3 C4 -29.6(4) . . . . ?
C1 C2 C3 C13 147.3(3) . . . . ?
C1 C2 C6 C7 173.8(2) . . . . ?
C1 C2 C6 O1 -63.7(3) . . . . ?
C2 C1 N1 C5 -56.1(3) . . . . ?
C2 C1 N1 C14 124.0(3) . . . . ?
C2 C3 C4 C5 -3.5(5) . . . . ?
C2 C6 C7 C8 -99.3(3) . . . . ?
C2 C6 C7 C12 77.4(3) . . . . ?
C3 C2 C6 C7 51.7(3) . . . . ?
C3 C2 C6 O1 174.2(2) . . . . ?
C3 C4 C5 N1 8.9(5) . . . . ?
C4 C5 N1 C1 22.4(4) . . . . ?
C4 C5 N1 C14 -157.7(3) . . . . ?
C6 C2 C3 C4 93.4(3) . . . . ?
C6 C2 C3 C13 -89.7(3) . . . . ?
C6 C7 C8 C9 176.4(3) . . . . ?
C6 C7 C12 C11 -175.9(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C7 -0.9(5) . . . . ?
C12 C7 C8 C9 -0.3(4) . . . . ?
C13 C3 C4 C5 179.6(3) . . . . ?
C15 C14 N1 C1 -0.6(4) . . . . ?
C15 C14 N1 C5 179.6(3) . . . . ?
N1 C1 C2 C3 57.8(3) . . . . ?
N1 C1 C2 C6 -67.7(3) . . . . ?
O1 C6 C7 C8 140.6(3) . . . . ?
O1 C6 C7 C12 -42.7(4) . . . . ?
O2 C14 N1 C1 -179.7(3) . . . . ?
O2 C14 N1 C5 0.4(4) . . . . ?
