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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/39/7113932.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_7113932
loop_
_publ_author_name
'Angel Manu Martinez'
'Nuria Rodriguez'
'Ramon Gomez Arrayas'
'Juan C. Carretero'
_publ_section_title
;
 Synthesis of alkylidene pyrrolo[3,4-b]pyridin-7-one derivatives via
 RhIII-catalyzed cascade oxidative alkenylation/annulation of
 picolinamides
;
_journal_name_full               Chem.Commun.
_journal_page_first              6105
_journal_paper_doi               10.1039/C4CC02322F
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_chemical_name_common            rzg1561
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.544(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5891(13)
_cell_length_b                   11.2221(16)
_cell_length_c                   17.124(3)
_cell_measurement_reflns_used    2836
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.0768
_cell_measurement_theta_min      2.9263
_cell_volume                     1458.3(4)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10397
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.376
_refine_ls_extinction_coef       0.020(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.1108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1773P)²+4.1421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3595
_refine_ls_wR_factor_ref         0.3853
_reflns_number_gt                1864
_reflns_number_total             2659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc02322f2.cif
_cod_data_source_block           I_a
_cod_database_code               7113932
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.7465(8) 0.0804(5) 0.0276(3) 0.0458(14) Uani d . 1
C C2 0.7821(10) 0.0558(6) -0.0494(4) 0.0581(17) Uani d . 1
H H2 0.7821 -0.0217 -0.0686 0.07 Uiso calc R 1
C C3 0.8170(12) 0.1500(7) -0.0954(4) 0.074(2) Uani d . 1
H H3 0.8429 0.1372 -0.1477 0.089 Uiso calc R 1
C C4 0.8154(11) 0.2657(7) -0.0669(5) 0.073(2) Uani d . 1
H H4 0.8358 0.3278 -0.1017 0.088 Uiso calc R 1
C C6 0.7518(8) 0.1991(5) 0.0524(4) 0.0503(15) Uani d . 1
C C7 0.7124(8) 0.2050(5) 0.1366(4) 0.0525(16) Uani d . 1
C C8 0.7025(8) 0.0082(5) 0.0980(3) 0.0433(13) Uani d . 1
C C9 0.6496(8) 0.0586(6) 0.2407(3) 0.0522(16) Uani d . 1
H H9A 0.6928 0.1222 0.2742 0.063 Uiso calc R 1
H H9B 0.7139 -0.0133 0.2542 0.063 Uiso calc R 1
C C10 0.4559(8) 0.0392(5) 0.2563(3) 0.0451(14) Uani d . 1
C C11 0.3278(9) 0.1107(7) 0.2272(4) 0.0629(18) Uani d . 1
H H11 0.3575 0.1726 0.1937 0.075 Uiso calc R 1
C C12 0.1537(10) 0.0930(9) 0.2464(5) 0.083(2) Uani d . 1
H H12 0.0669 0.1411 0.2243 0.1 Uiso calc R 1
C C13 0.1086(11) 0.0066(9) 0.2968(5) 0.081(2) Uani d . 1
H H13 -0.0084 -0.003 0.3111 0.097 Uiso calc R 1
C C14 0.2363(10) -0.0671(6) 0.3270(4) 0.0620(18) Uani d . 1
H H14 0.2055 -0.1279 0.3612 0.074 Uiso calc R 1
C C15 0.4082(9) -0.0515(6) 0.3069(4) 0.0559(17) Uani d . 1
H H15 0.4941 -0.102 0.3274 0.067 Uiso calc R 1
C C16 0.6848(9) -0.1084(5) 0.1110(3) 0.0517(16) Uani d . 1
H H16 0.6589 -0.1309 0.1619 0.062 Uiso calc R 1
C C17 0.7018(9) -0.2061(5) 0.0535(4) 0.0502(15) Uani d . 1
C C18 0.7291(15) -0.4146(6) 0.0413(4) 0.084(3) Uani d . 1
H H18A 0.6237 -0.4236 0.0105 0.127 Uiso calc R 1
H H18B 0.7448 -0.4836 0.0739 0.127 Uiso calc R 1
H H18C 0.8285 -0.4064 0.0075 0.127 Uiso calc R 1
N N1 0.7863(8) 0.2924(5) 0.0067(4) 0.0663(16) Uani d . 1
N N2 0.6853(6) 0.0895(4) 0.1588(3) 0.0471(12) Uani d . 1
O O1 0.7073(7) 0.2917(4) 0.1789(3) 0.0731(16) Uani d . 1
O O2 0.7038(10) -0.1970(4) -0.0170(3) 0.0833(19) Uani d . 1
O O3 0.7144(8) -0.3098(4) 0.0897(3) 0.0669(15) Uani d . 1
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
C2 C1 C6 118.5(6)
C2 C1 C8 135.4(6)
C6 C1 C8 106.1(5)
C3 C2 C1 116.4(6)
C2 C3 C4 121.8(7)
N1 C4 C3 123.4(7)
N1 C6 C1 125.1(6)
N1 C6 C7 125.4(6)
C1 C6 C7 109.5(5)
O1 C7 N2 126.0(6)
O1 C7 C6 128.8(6)
N2 C7 C6 105.2(5)
C16 C8 N2 120.6(5)
C16 C8 C1 133.6(5)
N2 C8 C1 105.8(5)
N2 C9 C10 113.0(5)
C11 C10 C15 118.4(6)
C11 C10 C9 123.1(6)
C15 C10 C9 118.5(6)
C10 C11 C12 120.9(7)
C13 C12 C11 120.5(8)
C12 C13 C14 119.6(7)
C15 C14 C13 120.1(7)
C14 C15 C10 120.5(7)
C8 C16 C17 127.3(6)
O2 C17 O3 122.7(5)
O2 C17 C16 127.1(5)
O3 C17 C16 110.2(5)
C4 N1 C6 114.8(6)
C7 N2 C8 113.4(5)
C7 N2 C9 121.2(5)
C8 N2 C9 125.3(5)
C17 O3 C18 116.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.375(9)
C1 C6 1.398(8)
C1 C8 1.494(8)
C2 C3 1.347(10)
C3 C4 1.387(11)
C4 N1 1.317(10)
C6 N1 1.334(8)
C6 C7 1.477(9)
C7 O1 1.214(7)
C7 N2 1.367(8)
C8 C16 1.334(9)
C8 N2 1.391(7)
C9 N2 1.472(8)
C9 C10 1.513(9)
C10 C11 1.352(9)
C10 C15 1.387(8)
C11 C12 1.379(11)
C12 C13 1.344(12)
C13 C14 1.372(12)
C14 C15 1.363(10)
C16 C17 1.480(8)
C17 O2 1.211(7)
C17 O3 1.323(7)
C18 O3 1.444(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101875470
