#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/12/7111233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111233
loop_
_publ_author_name
'Sierra, Miguel A.'
'del Amo, Juan C.'
'Mancheño, María J.'
'Gómez-Gallego, Mar'
'Torres, M. Rosario'
_publ_section_title
;
 New Pd-catalyzed tandem cyclization processes on group 6 bis-carbene
 complexes
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1842
_journal_page_last               1843
_journal_paper_doi               10.1039/b204907d
_journal_year                    2002
_chemical_formula_sum            'C26 H22 N2 O2'
_chemical_formula_weight         394.46
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 129.124(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.815(3)
_cell_length_b                   10.6199(13)
_cell_length_c                   18.243(2)
_cell_measurement_temperature    296(2)
_cell_volume                     4180.6(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0921
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10720
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.0418P)²+0.0000P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1761
_reflns_number_total             3682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204907dsup1.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        4180.6(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7111233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N1 N 0.22452(10) 0.28212(18) 0.11030(16) 0.0429(5) Uani 1 1 d .
C2 C 0.22810(12) 0.2931(2) 0.19256(19) 0.0417(7) Uani 1 1 d .
C3 C 0.27049(13) 0.2194(2) 0.2714(2) 0.0520(8) Uani 1 1 d .
H3 H 0.2965 0.1590 0.2590 0.071(8) Uiso 1 1 d R
C4 C 0.27370(14) 0.2249(2) 0.3503(2) 0.0573(8) Uani 1 1 d .
H4 H 0.3100 0.1769 0.4078 0.060(8) Uiso 1 1 d R
C5 C 0.23449(13) 0.3038(2) 0.3512(2) 0.0539(8) Uani 1 1 d .
H5 H 0.2349 0.3033 0.4110 0.074(8) Uiso 1 1 d R
C6 C 0.19242(12) 0.3762(2) 0.27268(19) 0.0470(7) Uani 1 1 d .
H6 H 0.1620 0.4333 0.2690 0.042(6) Uiso 1 1 d R
C7 C 0.18756(12) 0.3736(2) 0.19161(18) 0.0402(6) Uani 1 1 d .
N8 N 0.14153(10) 0.45412(18) 0.12027(16) 0.0419(5) Uani 1 1 d .
C9 C 0.11438(12) 0.4614(2) 0.0318(2) 0.0405(6) Uani 1 1 d .
C10 C 0.12777(12) 0.3844(2) -0.02415(19) 0.0440(7) Uani 1 1 d .
H10 H 0.0863 0.3628 -0.0913 0.051(7) Uiso 1 1 d R
C11 C 0.16694(14) 0.4621(3) -0.0407(2) 0.0532(8) Uani 1 1 d .
C12 C 0.23294(13) 0.4401(2) 0.0255(2) 0.0522(7) Uani 1 1 d .
H12 H 0.2573 0.4857 0.0053 0.065(8) Uiso 1 1 d R
C13 C 0.26021(12) 0.3646(2) 0.10186(19) 0.0449(7) Uani 1 1 d .
C14 C 0.16182(13) 0.2614(2) 0.0203(2) 0.0475(7) Uani 1 1 d .
H14 H 0.1711 0.2180 -0.0230 0.051(7) Uiso 1 1 d R
O15 O 0.12662(8) 0.18457(15) 0.03263(13) 0.0526(5) Uani 1 1 d .
C16 C 0.14431(15) 0.0537(2) 0.0482(3) 0.0753(10) Uani 1 1 d .
H16A H 0.1859 0.0445 0.1078 0.090 Uiso 1 1 calc R
H16B H 0.1444 0.0235 -0.0019 0.090 Uiso 1 1 calc R
C17 C 0.10205(19) -0.0189(3) 0.0502(4) 0.1358(18) Uani 1 1 d .
H17A H 0.1145 -0.1057 0.0614 0.204 Uiso 1 1 calc R
H17B H 0.0611 -0.0111 -0.0094 0.204 Uiso 1 1 calc R
H17C H 0.1021 0.0113 0.0998 0.204 Uiso 1 1 calc R
C18 C 0.06279(12) 0.5556(2) -0.02288(19) 0.0409(6) Uani 1 1 d .
C19 C 0.04877(12) 0.6274(2) 0.0252(2) 0.0524(7) Uani 1 1 d .
H19 H 0.0768 0.6201 0.0982 0.060(8) Uiso 1 1 d R
C20 C -0.00017(14) 0.7112(3) -0.0221(2) 0.0607(8) Uani 1 1 d .
H20 H -0.0141 0.7612 0.0108 0.078(9) Uiso 1 1 d R
C21 C -0.03655(14) 0.7247(3) -0.1184(2) 0.0594(8) Uani 1 1 d .
H21 H -0.0753 0.7868 -0.1584 0.082(9) Uiso 1 1 d R
C22 C -0.02322(14) 0.6553(3) -0.1675(2) 0.0655(8) Uani 1 1 d .
H22 H -0.0516 0.6618 -0.2409 0.102(11) Uiso 1 1 d R
C23 C 0.02596(13) 0.5716(3) -0.1205(2) 0.0560(8) Uani 1 1 d .
H23 H 0.0399 0.5117 -0.1502 0.094(10) Uiso 1 1 d R
O24 O 0.14345(10) 0.5389(2) -0.10490(16) 0.0767(7) Uani 1 1 d .
C25 C 0.32839(13) 0.3573(3) 0.17359(19) 0.0481(7) Uani 1 1 d .
C26 C 0.36418(15) 0.4671(3) 0.2030(2) 0.0669(9) Uani 1 1 d .
H26 H 0.3403 0.5539 0.1593 0.146(14) Uiso 1 1 d R
C27 C 0.42834(17) 0.4577(4) 0.2618(3) 0.0810(10) Uani 1 1 d .
H27 H 0.4541 0.5404 0.2839 0.115(12) Uiso 1 1 d R
C28 C 0.45642(18) 0.3418(4) 0.2918(2) 0.0842(11) Uani 1 1 d .
H28 H 0.5008 0.3370 0.3342 0.105(12) Uiso 1 1 d R
C29 C 0.42210(15) 0.2334(3) 0.2639(2) 0.0666(9) Uani 1 1 d .
H29 H 0.4440 0.1423 0.2877 0.084(9) Uiso 1 1 d R
C30 C 0.35800(14) 0.2412(3) 0.2053(2) 0.0532(8) Uani 1 1 d .
H30 H 0.3310 0.1605 0.1798 0.059(8) Uiso 1 1 d 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
C13 N1 C2 118.3(2)
C13 N1 C14 113.1(2)
C2 N1 C14 115.28(19)
C7 C2 C3 120.3(2)
C7 C2 N1 120.5(2)
C3 C2 N1 119.2(2)
C4 C3 C2 120.5(2)
C4 C3 H3 128.5
C2 C3 H3 110.9
C3 C4 C5 120.2(3)
C3 C4 H4 114.8
C5 C4 H4 124.5
C6 C5 C4 119.0(3)
C6 C5 H5 120.8
C4 C5 H5 120.1
C5 C6 C7 122.7(2)
C5 C6 H6 122.1
C7 C6 H6 115.2
N8 C7 C6 113.1(2)
N8 C7 C2 129.7(2)
C6 C7 C2 117.2(2)
C9 N8 C7 132.3(2)
N8 C9 C18 115.7(2)
N8 C9 C10 127.7(2)
C18 C9 C10 116.6(2)
C9 C10 C14 116.0(2)
C9 C10 C11 110.2(2)
C14 C10 C11 106.6(2)
C9 C10 H10 110.3
C14 C10 H10 106.9
C11 C10 H10 106.2
O24 C11 C12 122.5(3)
O24 C11 C10 121.9(3)
C12 C11 C10 115.6(2)
C13 C12 C11 123.3(3)
C13 C12 H12 123.9
C11 C12 H12 112.7
C12 C13 N1 120.5(3)
C12 C13 C25 121.1(2)
N1 C13 C25 118.2(2)
O15 C14 N1 111.4(2)
O15 C14 C10 109.0(2)
N1 C14 C10 111.6(2)
O15 C14 H14 112.6
N1 C14 H14 102.6
C10 C14 H14 109.6
C14 O15 C16 114.09(19)
O15 C16 C17 110.0(2)
O15 C16 H16A 109.7
C17 C16 H16A 109.7
O15 C16 H16B 109.7
C17 C16 H16B 109.7
H16A C16 H16B 108.2
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 C23 117.8(3)
C19 C18 C9 118.5(2)
C23 C18 C9 123.6(2)
C20 C19 C18 121.1(3)
C20 C19 H19 119.7
C18 C19 H19 119.1
C21 C20 C19 120.4(3)
C21 C20 H20 116.3
C19 C20 H20 123.1
C20 C21 C22 119.5(3)
C20 C21 H21 123.4
C22 C21 H21 117.1
C23 C22 C21 120.5(3)
C23 C22 H22 119.2
C21 C22 H22 120.2
C22 C23 C18 120.7(3)
C22 C23 H23 127.5
C18 C23 H23 111.8
C30 C25 C26 119.2(3)
C30 C25 C13 120.5(3)
C26 C25 C13 120.0(3)
C27 C26 C25 119.5(3)
C27 C26 H26 120.2
C25 C26 H26 117.0
C28 C27 C26 120.1(3)
C28 C27 H27 121.5
C26 C27 H27 118.3
C27 C28 C29 121.1(4)
C27 C28 H28 119.2
C29 C28 H28 119.7
C28 C29 C30 119.4(3)
C28 C29 H29 121.3
C30 C29 H29 119.3
C25 C30 C29 120.7(3)
C25 C30 H30 118.4
C29 C30 H30 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C13 1.403(3)
N1 C2 1.445(3)
N1 C14 1.474(3)
C2 C7 1.406(3)
C2 C3 1.390(3)
C3 C4 1.386(3)
C3 H3 1.0918
C4 C5 1.383(3)
C4 H4 1.0213
C5 C6 1.377(3)
C5 H5 1.0842
C6 C7 1.398(3)
C6 H6 1.0080
C7 N8 1.400(3)
N8 C9 1.282(3)
C9 C18 1.500(3)
C9 C10 1.525(3)
C10 C14 1.514(3)
C10 C11 1.540(3)
C10 H10 1.0490
C11 O24 1.224(3)
C11 C12 1.444(4)
C12 C13 1.351(3)
C12 H12 1.0712
C13 C25 1.478(4)
C14 O15 1.398(3)
C14 H14 1.0776
O15 C16 1.441(3)
C16 C17 1.424(4)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.391(3)
C18 C23 1.396(3)
C19 C20 1.381(3)
C19 H19 1.0381
C20 C21 1.374(4)
C20 H20 1.0421
C21 C22 1.378(4)
C21 H21 1.0655
C22 C23 1.385(3)
C22 H22 1.0436
C23 H23 1.0555
C25 C30 1.390(3)
C25 C26 1.401(4)
C26 C27 1.389(4)
C26 H26 1.1224
C27 C28 1.373(4)
C27 H27 1.0402
C28 C29 1.372(4)
C28 H28 0.9601
C29 C30 1.387(4)
C29 H29 1.0773
C30 H30 1.0361
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
C13 N1 C2 C7 89.7(3)
C14 N1 C2 C7 -48.6(3)
C13 N1 C2 C3 -92.8(3)
C14 N1 C2 C3 128.9(2)
C7 C2 C3 C4 -0.4(4)
N1 C2 C3 C4 -178.0(2)
C2 C3 C4 C5 0.2(4)
C3 C4 C5 C6 0.1(4)
C4 C5 C6 C7 0.0(4)
C5 C6 C7 N8 179.7(2)
C5 C6 C7 C2 -0.2(4)
C3 C2 C7 N8 -179.4(2)
N1 C2 C7 N8 -1.9(4)
C3 C2 C7 C6 0.5(4)
N1 C2 C7 C6 178.0(2)
C6 C7 N8 C9 -164.0(3)
C2 C7 N8 C9 15.9(4)
C7 N8 C9 C18 174.9(2)
C7 N8 C9 C10 -4.1(4)
N8 C9 C10 C14 20.4(4)
C18 C9 C10 C14 -158.6(2)
N8 C9 C10 C11 -100.9(3)
C18 C9 C10 C11 80.1(3)
C9 C10 C11 O24 -82.3(3)
C14 C10 C11 O24 151.0(3)
C9 C10 C11 C12 96.5(3)
C14 C10 C11 C12 -30.2(3)
O24 C11 C12 C13 173.6(3)
C10 C11 C12 C13 -5.1(4)
C11 C12 C13 N1 13.6(4)
C11 C12 C13 C25 -172.5(2)
C2 N1 C13 C12 -122.6(3)
C14 N1 C13 C12 16.6(3)
C2 N1 C13 C25 63.4(3)
C14 N1 C13 C25 -157.4(2)
C13 N1 C14 O15 -176.66(18)
C2 N1 C14 O15 -36.2(3)
C13 N1 C14 C10 -54.6(3)
C2 N1 C14 C10 85.8(2)
C9 C10 C14 O15 59.7(3)
C11 C10 C14 O15 -177.2(2)
C9 C10 C14 N1 -63.7(3)
C11 C10 C14 N1 59.5(3)
N1 C14 O15 C16 -73.5(3)
C10 C14 O15 C16 163.0(2)
C14 O15 C16 C17 -174.0(3)
N8 C9 C18 C19 0.6(3)
C10 C9 C18 C19 179.7(2)
N8 C9 C18 C23 -176.4(2)
C10 C9 C18 C23 2.7(3)
C23 C18 C19 C20 0.4(4)
C9 C18 C19 C20 -176.8(2)
C18 C19 C20 C21 0.5(4)
C19 C20 C21 C22 -1.1(4)
C20 C21 C22 C23 0.8(4)
C21 C22 C23 C18 0.2(4)
C19 C18 C23 C22 -0.7(4)
C9 C18 C23 C22 176.3(2)
C12 C13 C25 C30 -132.0(3)
N1 C13 C25 C30 42.1(3)
C12 C13 C25 C26 41.4(3)
N1 C13 C25 C26 -144.5(2)
C30 C25 C26 C27 1.1(4)
C13 C25 C26 C27 -172.3(3)
C25 C26 C27 C28 -0.9(5)
C26 C27 C28 C29 0.7(5)
C27 C28 C29 C30 -0.7(4)
C26 C25 C30 C29 -1.2(4)
C13 C25 C30 C29 172.3(2)
C28 C29 C30 C25 0.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184003
