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#$Date: 2024-12-06 22:34:51 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296670 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160162.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_7160162
loop_
_publ_author_name
'Boruah, Aditi'
'Deb, Mohit L.'
'Thakuria, Ranjit'
'Baruah, Pranjal K.'
_publ_section_title
;
 L-Proline catalyzed multi-component synthesis of
 N-pyridyl-tetrahydroisoquinolines and their
 α-C(sp³)-H oxygenation.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8608
_journal_page_last               8616
_journal_paper_doi               10.1039/d4ob01343c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H17 N5'
_chemical_formula_sum            'C22 H17 N5'
_chemical_formula_weight         351.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.166(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.101(5)
_cell_length_b                   7.088(3)
_cell_length_c                   17.585(6)
_cell_measurement_reflns_used    1490
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.73
_cell_volume                     1858.6(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.747
_diffrn_measured_fraction_theta_max 0.644
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_Laue_measured_fraction_full 0.747
_diffrn_reflns_Laue_measured_fraction_max 0.644
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5939
_diffrn_reflns_point_group_measured_fraction_full 0.747
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.484
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0463
_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)+(0.0106P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1936
_reflns_number_total             3641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01343c2.cif
_cod_data_source_block           pn_01_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160161--7160162.cif.'
_cod_original_cell_volume        1858.6(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160162
_shelx_shelxl_version_number     2016/6
_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   0.985
_shelx_estimated_absorpt_t_max   0.989
_exptl_absorpt_special_details   Sheldrick,G.M.,(2003)
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.44947(10) 0.1910(2) 0.72228(9) 0.0395(5) Uani 1 1 d . . . . .
H1A H 0.467544 0.293798 0.761572 0.047 Uiso 1 1 calc R U . . .
H1B H 0.453946 0.074818 0.752691 0.047 Uiso 1 1 calc R U . . .
C2 C 0.35242(12) 0.2205(2) 0.66520(10) 0.0424(5) Uani 1 1 d . . . . .
C3 C 0.28857(14) 0.2431(2) 0.69954(13) 0.0556(6) Uani 1 1 d . . . . .
H3 H 0.305918 0.237050 0.756275 0.067 Uiso 1 1 calc R U . . .
C4 C 0.19921(13) 0.2745(3) 0.65090(16) 0.0725(7) Uani 1 1 d . . . . .
H4 H 0.157120 0.290965 0.674822 0.087 Uiso 1 1 calc R U . . .
C5 C 0.17322(15) 0.2811(3) 0.56631(17) 0.0792(8) Uani 1 1 d . . . . .
H5 H 0.113359 0.300373 0.532971 0.095 Uiso 1 1 calc R U . . .
C6 C 0.23612(15) 0.2590(3) 0.53215(13) 0.0691(7) Uani 1 1 d . . . . .
H6 H 0.218269 0.265639 0.475381 0.083 Uiso 1 1 calc R U . . .
C7 C 0.32709(12) 0.2264(2) 0.58043(11) 0.0516(6) Uani 1 1 d . . . . .
C8 C 0.39488(12) 0.1933(3) 0.54202(9) 0.0568(6) Uani 1 1 d . . . . .
H8A H 0.415964 0.313346 0.529799 0.068 Uiso 1 1 calc R U . . .
H8B H 0.367170 0.124629 0.490919 0.068 Uiso 1 1 calc R U . . .
C9 C 0.47361(9) 0.0809(2) 0.60031(7) 0.0438(5) Uani 1 1 d . . . . .
H9A H 0.453825 -0.044047 0.608515 0.053 Uiso 1 1 calc R U . . .
H9B H 0.519323 0.067221 0.577242 0.053 Uiso 1 1 calc R U . . .
C10 C 0.60082(11) 0.2060(2) 0.72249(8) 0.0324(5) Uani 1 1 d . . . . .
C11 C 0.66334(11) 0.2320(2) 0.68459(8) 0.0351(5) Uani 1 1 d . . . . .
C12 C 0.75576(11) 0.2487(2) 0.73358(8) 0.0360(5) Uani 1 1 d . . . . .
C13 C 0.78040(11) 0.2477(2) 0.81846(8) 0.0353(5) Uani 1 1 d . . . . .
C14 C 0.71347(12) 0.2342(2) 0.85142(8) 0.0345(5) Uani 1 1 d . . . . .
C15 C 0.63645(11) 0.2746(2) 0.59863(9) 0.0439(5) Uani 1 1 d . . . . .
C16 C 0.82345(12) 0.2689(3) 0.69602(9) 0.0436(5) Uani 1 1 d . . . . .
C17 C 0.84047(14) 0.1227(3) 0.65253(11) 0.0666(6) Uani 1 1 d . . . . .
H17 H 0.809240 0.009896 0.647104 0.080 Uiso 1 1 calc R U . . .
C18 C 0.90314(18) 0.1404(5) 0.61677(12) 0.0869(8) Uani 1 1 d . . . . .
H18 H 0.914991 0.039397 0.588668 0.104 Uiso 1 1 calc R U . . .
C19 C 0.94784(15) 0.3084(6) 0.62300(13) 0.0984(10) Uani 1 1 d . . . . .
H19 H 0.988488 0.322724 0.597345 0.118 Uiso 1 1 calc R U . . .
C20 C 0.93260(16) 0.4551(5) 0.66701(16) 0.1016(9) Uani 1 1 d . . . . .
H20 H 0.963730 0.567958 0.672105 0.122 Uiso 1 1 calc R U . . .
C21 C 0.87093(15) 0.4347(3) 0.70368(12) 0.0785(7) Uani 1 1 d . . . . .
H21 H 0.861242 0.533951 0.733944 0.094 Uiso 1 1 calc R U . . .
C22 C 0.87323(11) 0.2586(2) 0.87238(9) 0.0479(5) Uani 1 1 d . . . . .
H3A H 0.7981(4) 0.257(2) 0.9696(10) 0.086(7) Uiso 1 1 d D . . . .
H3B H 0.6876(9) 0.221(3) 0.9591(10) 0.096(8) Uiso 1 1 d D . . . .
N1 N 0.51064(8) 0.18177(18) 0.67930(6) 0.0384(4) Uani 1 1 d . . . . .
N2 N 0.62546(8) 0.21203(16) 0.80441(6) 0.0355(4) Uani 1 1 d . . . . .
N3 N 0.73304(10) 0.2397(2) 0.93288(7) 0.0482(4) Uani 1 1 d D . . . .
N4 N 0.61493(10) 0.3120(2) 0.53104(7) 0.0632(5) Uani 1 1 d . . . . .
N5 N 0.94582(10) 0.2659(2) 0.91852(9) 0.0738(6) Uani 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 0.0033 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'
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
N1 C1 C2 113.14(14) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 119.92(17) . . ?
C3 C2 C1 118.40(16) . . ?
C7 C2 C1 121.68(19) . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 119.60(19) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C2 C7 C6 118.0(2) . . ?
C2 C7 C8 120.54(15) . . ?
C6 C7 C8 121.44(18) . . ?
C7 C8 C9 109.95(14) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C8 108.60(14) . . ?
N1 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 N1 114.86(16) . . ?
N2 C10 C11 121.80(13) . . ?
N1 C10 C11 123.28(12) . . ?
C10 C11 C12 119.75(13) . . ?
C10 C11 C15 122.50(14) . . ?
C12 C11 C15 116.90(17) . . ?
C13 C12 C11 117.45(18) . . ?
C13 C12 C16 121.29(14) . . ?
C11 C12 C16 121.26(13) . . ?
C12 C13 C14 119.31(14) . . ?
C12 C13 C22 120.75(18) . . ?
C14 C13 C22 119.94(13) . . ?
N3 C14 N2 115.09(19) . . ?
N3 C14 C13 121.91(14) . . ?
N2 C14 C13 123.00(13) . . ?
N4 C15 C11 178.59(18) . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 C12 120.71(18) . . ?
C21 C16 C12 120.83(18) . . ?
C16 C17 C18 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
N5 C22 C13 176.60(19) . . ?
C10 N1 C1 119.37(11) . . ?
C10 N1 C9 123.35(13) . . ?
C1 N1 C9 113.58(12) . . ?
C10 N2 C14 118.45(16) . . ?
C14 N3 H3A 117.0(12) . . ?
C14 N3 H3B 124.2(11) . . ?
H3A N3 H3B 118.7(17) . . ?
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 N1 1.452(2) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.384(3) . ?
C2 C7 1.390(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.503(3) . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.4737(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.3429(18) . ?
C10 N1 1.3719(19) . ?
C10 C11 1.413(3) . ?
C11 C12 1.415(2) . ?
C11 C15 1.439(2) . ?
C12 C13 1.392(2) . ?
C12 C16 1.479(3) . ?
C13 C14 1.406(2) . ?
C13 C22 1.439(2) . ?
C14 N3 1.346(2) . ?
C14 N2 1.354(2) . ?
C15 N4 1.1368(19) . ?
C16 C17 1.375(3) . ?
C16 C21 1.381(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N5 1.1452(19) . ?
N3 H3A 1.0096(11) . ?
N3 H3B 1.0099(11) . ?
