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#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515967.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_1515967
loop_
_publ_author_name
'Graham, Thomas J. A.'
'Shields, Jason D.'
'Doyle, Abigail G.'
_publ_section_title
;
 Transition metal-catalyzed cross coupling with N-acyliminium ions derived
 from quinolines and isoquinolines
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              980
_journal_paper_doi               10.1039/c1sc00026h
_journal_volume                  2
_journal_year                    2011
_chemical_formula_sum            'C23 H23 N2 O3'
_chemical_formula_weight         375.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0405(3)
_cell_length_b                   17.1549(4)
_cell_length_c                   10.0631(3)
_cell_measurement_temperature    296(1)
_cell_volume                     2078.52(9)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            36138
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0675P)²+0.5956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                3058
_reflns_number_total             3689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00026h.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               1515967
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23839(17) 0.34926(10) 0.8690(2) 0.0697(6) Uani 1 1 d . . .
H1 H 0.2117 0.2966 0.8484 0.093 Uiso 1 1 calc R . .
C2 C 0.17078(18) 0.37839(12) 0.9822(3) 0.0768(6) Uani 1 1 d . . .
H2 H 0.1524 0.3443 1.0504 0.102 Uiso 1 1 calc R . .
C3 C 0.13632(16) 0.45152(11) 0.9881(2) 0.0649(5) Uani 1 1 d . . .
H3 H 0.0926 0.4675 1.0589 0.086 Uiso 1 1 calc R . .
C4 C 0.16594(13) 0.50733(9) 0.88544(17) 0.0474(4) Uani 1 1 d . . .
C5 C 0.15184(13) 0.58696(9) 0.90305(15) 0.0442(4) Uani 1 1 d . . .
H5 H 0.1205 0.6053 0.9812 0.059 Uiso 1 1 calc R . .
C6 C 0.18362(13) 0.63943(9) 0.80644(14) 0.0429(4) Uani 1 1 d . . .
C7 C 0.23379(15) 0.61195(10) 0.69219(16) 0.0510(4) Uani 1 1 d . . .
H7 H 0.2585 0.6468 0.6281 0.068 Uiso 1 1 calc R . .
C8 C 0.24717(15) 0.53269(10) 0.67332(16) 0.0536(4) Uani 1 1 d . . .
H8 H 0.2814 0.5146 0.5967 0.071 Uiso 1 1 calc R . .
C9 C 0.21033(13) 0.48007(9) 0.76697(17) 0.0487(4) Uani 1 1 d . . .
C10 C 0.14439(16) 0.77552(10) 0.74079(17) 0.0545(4) Uani 1 1 d . . .
C11 C 0.1253(2) 0.85571(12) 0.7967(2) 0.0854(7) Uani 1 1 d . . .
H11a H 0.1861 0.8890 0.7732 0.128 Uiso 1 1 calc R . .
H11b H 0.1201 0.8526 0.8917 0.128 Uiso 1 1 calc R . .
H11c H 0.0575 0.8766 0.7608 0.128 Uiso 1 1 calc R . .
C12 C 0.36205(17) 0.34253(11) 0.8980(2) 0.0655(5) Uani 1 1 d . . .
C13 C 0.4148(2) 0.38785(15) 0.9911(3) 0.0866(7) Uani 1 1 d . . .
H13 H 0.3742 0.4237 1.0402 0.115 Uiso 1 1 calc R . .
C14 C 0.5283(2) 0.3808(2) 1.0128(3) 0.1065(9) Uani 1 1 d . . .
H14 H 0.5632 0.4120 1.0762 0.142 Uiso 1 1 calc R . .
C15 C 0.5887(2) 0.3287(2) 0.9420(3) 0.1037(9) Uani 1 1 d . . .
H15 H 0.6647 0.3239 0.9574 0.138 Uiso 1 1 calc R . .
C16 C 0.5381(2) 0.28362(17) 0.8485(3) 0.0998(8) Uani 1 1 d . . .
H16 H 0.5796 0.2481 0.7997 0.133 Uiso 1 1 calc R . .
C17 C 0.4249(2) 0.29035(13) 0.8257(3) 0.0846(7) Uani 1 1 d . . .
H17 H 0.3909 0.2595 0.7612 0.112 Uiso 1 1 calc R . .
C21 C 0.5302(3) 0.4710(3) 0.6199(4) 0.1347(14) Uani 1 1 d D . .
H21 H 0.5508 0.4512 0.7025 0.179 Uiso 1 1 calc R . .
C22 C 0.5395(3) 0.5493(3) 0.5950(4) 0.1312(12) Uani 1 1 d D . .
H22 H 0.5668 0.5827 0.6603 0.174 Uiso 1 1 calc R . .
C23 C 0.5087(4) 0.5775(2) 0.4749(5) 0.1315(13) Uani 1 1 d D . .
H23 H 0.5144 0.6306 0.4576 0.175 Uiso 1 1 calc R . .
O1 O 0.14244(14) 0.76328(8) 0.62170(12) 0.0723(4) Uani 1 1 d . . .
C18 C 0.1885(2) 0.35882(13) 0.6384(3) 0.0972(9) Uani 1 1 d DU . .
O2 O 0.2115(7) 0.2922(4) 0.6052(8) 0.113(3) Uani 0.55 1 d PDU A 1
O3 O 0.1343(4) 0.4040(3) 0.5574(4) 0.0707(12) Uani 0.55 1 d PDU A 1
C19 C 0.1138(6) 0.3638(2) 0.4328(4) 0.0760(12) Uani 0.55 1 d PDU A 1
H19a H 0.0552 0.3255 0.4425 0.101 Uiso 0.55 1 calc PR A 1
H19b H 0.1805 0.3376 0.4026 0.101 Uiso 0.55 1 calc PR A 1
C20 C 0.0805(7) 0.4246(3) 0.3394(6) 0.1024(19) Uani 0.55 1 d PDU A 1
H20a H 0.0633 0.4016 0.2547 0.154 Uiso 0.55 1 calc PR A 1
H20b H 0.1402 0.4612 0.3294 0.154 Uiso 0.55 1 calc PR A 1
H20c H 0.0162 0.4511 0.3725 0.154 Uiso 0.55 1 calc PR A 1
O2' O 0.1723(9) 0.2873(4) 0.6447(10) 0.096(3) Uani 0.45 1 d PDU A 2
O3' O 0.1806(5) 0.4133(4) 0.5225(5) 0.094(2) Uani 0.45 1 d PDU A 2
C19' C 0.1762(6) 0.3907(5) 0.3743(7) 0.108(2) Uani 0.45 1 d PDU A 2
H19a' H 0.1982 0.4335 0.3173 0.144 Uiso 0.45 1 calc PR A 2
H19b' H 0.2216 0.3453 0.3556 0.144 Uiso 0.45 1 calc PR A 2
C20' C 0.0597(8) 0.3740(8) 0.3627(14) 0.174(5) Uani 0.45 1 d PDU A 2
H20a' H 0.0438 0.3541 0.2754 0.261 Uiso 0.45 1 calc PR A 2
H20b' H 0.0179 0.4208 0.3771 0.261 Uiso 0.45 1 calc PR A 2
H20c' H 0.0395 0.3357 0.4279 0.261 Uiso 0.45 1 calc PR A 2
N1 N 0.21686(13) 0.39754(8) 0.75018(17) 0.0634(4) Uani 1 1 d . A .
N2 N 0.16507(13) 0.71963(7) 0.83155(13) 0.0502(4) Uani 1 1 d . . .
H2A H 0.1672 0.7341 0.9133 0.067 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
N1 C1 C2 109.71(15) .
N1 C1 C12 111.36(17) .
C2 C1 C12 114.72(19) .
C3 C2 C1 121.68(19) .
C2 C3 C4 120.90(19) .
C5 C4 C9 119.23(15) .
C5 C4 C3 121.74(16) .
C9 C4 C3 119.02(16) .
C6 C5 C4 121.12(15) .
C5 C6 C7 119.15(14) .
C5 C6 N2 117.55(14) .
C7 C6 N2 123.28(14) .
C8 C7 C6 120.04(15) .
C9 C8 C7 120.73(15) .
C8 C9 C4 119.51(15) .
C8 C9 N1 123.32(16) .
C4 C9 N1 117.16(16) .
O1 C10 N2 123.20(16) .
O1 C10 C11 121.60(16) .
N2 C10 C11 115.20(15) .
C13 C12 C17 118.3(2) .
C13 C12 C1 122.5(2) .
C17 C12 C1 119.2(2) .
C12 C13 C14 120.6(2) .
C15 C14 C13 120.4(3) .
C14 C15 C16 119.9(3) .
C15 C16 C17 120.2(3) .
C12 C17 C16 120.6(2) .
C23 C21 C22 120.3(4) 3_666
C23 C22 C21 119.5(4) .
C21 C23 C22 120.2(4) 3_666
O2 C18 O3 120.0(5) .
O2 C18 N1 129.2(5) .
O2' C18 N1 118.8(6) .
O3 C18 N1 110.7(3) .
O2' C18 O3' 130.3(6) .
N1 C18 O3' 110.9(3) .
C18 O3 C19 109.9(4) .
O3 C19 C20 105.1(4) .
C18 O3' C19' 126.8(5) .
C20' C19' O3' 98.9(8) .
C18 N1 C9 124.97(17) .
C18 N1 C1 116.21(17) .
C9 N1 C1 118.04(15) .
C10 N2 C6 126.82(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.476(3) .
C1 C2 1.491(3) .
C1 C12 1.520(3) .
C2 C3 1.323(3) .
C3 C4 1.455(2) .
C4 C5 1.388(2) .
C4 C9 1.391(2) .
C5 C6 1.381(2) .
C6 C7 1.385(2) .
C6 N2 1.417(2) .
C7 C8 1.382(2) .
C8 C9 1.380(2) .
C9 N1 1.428(2) .
C10 O1 1.217(2) .
C10 N2 1.346(2) .
C10 C11 1.504(3) .
C12 C13 1.371(3) .
C12 C17 1.382(3) .
C13 C14 1.388(4) .
C14 C15 1.357(4) .
C15 C16 1.359(4) .
C16 C17 1.385(4) .
C21 C23 1.347(6) 3_666
C21 C22 1.372(5) .
C22 C23 1.351(5) .
C23 C21 1.347(6) 3_666
C18 O2 1.223(6) .
C18 O2' 1.245(7) .
C18 O3 1.297(5) .
C18 N1 1.349(3) .
C18 O3' 1.497(6) .
O3 C19 1.451(5) .
C19 C20 1.459(6) .
O3' C19' 1.541(7) .
C19' C20' 1.436(8) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043328
