#------------------------------------------------------------------------------
#$Date: 2015-11-17 08:11:05 +0200 (Tue, 17 Nov 2015) $
#$Revision: 170361 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118063.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_7118063
loop_
_publ_author_name
'Qiang Dai'
'Yan Jiang'
'Jin-Tao Yu'
'Jiang Cheng'
_publ_section_title
;
 Palladium-catalyzed three-component reaction of N-tosyl hydrazones,
 isonitriles and amines leading to amidines
;
_journal_name_full               Chem.Commun.
_journal_page_first              16645
_journal_paper_doi               10.1039/C5cc06771E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C18 H20 N2 O'
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-09-08 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.546(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.471(3)
_cell_length_b                   18.936(8)
_cell_length_c                   9.695(4)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1533.6(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_laue_measured_fraction_full 0.990
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8145
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.386
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.125(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0466
_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)+(0.0929P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2206
_reflns_number_total             2670
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc06771e2.cif
_cod_data_source_block           complex5
_cod_original_cell_volume        1533.5(11)
_cod_database_code               7118063
_shelx_shelxl_version_number     2014/7
_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   0.970
_shelx_estimated_absorpt_t_max   0.970
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
O1 O 0.28673(16) 0.72174(6) 1.02525(13) 0.0731(4) Uani 1 1 d . . . . .
N1 N 0.15881(13) 0.48842(6) 0.85597(12) 0.0441(3) Uani 1 1 d . . . . .
N2 N 0.18154(16) 0.60796(6) 0.84737(13) 0.0519(4) Uani 1 1 d . . . . .
C1 C 0.19496(14) 0.54319(6) 0.78952(13) 0.0382(3) Uani 1 1 d . . . . .
C2 C 0.16114(16) 0.42034(7) 0.79820(14) 0.0419(4) Uani 1 1 d . . . . .
C3 C 0.27627(19) 0.37229(8) 0.85713(17) 0.0560(4) Uani 1 1 d . . . . .
H3 H 0.3536 0.3861 0.9319 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2779(2) 0.30421(8) 0.8064(2) 0.0667(5) Uani 1 1 d . . . . .
H4 H 0.3571 0.2729 0.8462 0.080 Uiso 1 1 calc R U . . .
C5 C 0.1633(2) 0.28252(9) 0.6978(2) 0.0656(5) Uani 1 1 d . . . . .
H5 H 0.1650 0.2367 0.6633 0.079 Uiso 1 1 calc R U . . .
C6 C 0.0463(2) 0.32889(9) 0.64037(18) 0.0610(5) Uani 1 1 d . . . . .
H6 H -0.0322 0.3142 0.5673 0.073 Uiso 1 1 calc R U . . .
C7 C 0.04408(17) 0.39726(8) 0.69019(16) 0.0517(4) Uani 1 1 d . . . . .
H7 H -0.0366 0.4280 0.6510 0.062 Uiso 1 1 calc R U . . .
C8 C 0.25422(16) 0.54120(7) 0.65115(14) 0.0433(4) Uani 1 1 d . . . . .
H8A H 0.2351 0.4944 0.6114 0.052 Uiso 1 1 calc R U . . .
H8B H 0.1915 0.5742 0.5879 0.052 Uiso 1 1 calc R U . . .
C9 C 0.42880(16) 0.55872(6) 0.65819(13) 0.0389(3) Uani 1 1 d . . . . .
C10 C 0.47894(18) 0.59504(8) 0.54950(15) 0.0505(4) Uani 1 1 d . . . . .
H10 H 0.4040 0.6095 0.4735 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6394(2) 0.61017(9) 0.5524(2) 0.0632(5) Uani 1 1 d . . . . .
H11 H 0.6714 0.6346 0.4786 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7511(2) 0.58931(10) 0.6636(2) 0.0659(5) Uani 1 1 d . . . . .
H12 H 0.8587 0.5998 0.6655 0.079 Uiso 1 1 calc R U . . .
C13 C 0.70393(19) 0.55299(9) 0.7720(2) 0.0647(5) Uani 1 1 d . . . . .
H13 H 0.7796 0.5384 0.8473 0.078 Uiso 1 1 calc R U . . .
C14 C 0.54356(18) 0.53799(8) 0.76928(16) 0.0515(4) Uani 1 1 d . . . . .
H14 H 0.5124 0.5135 0.8435 0.062 Uiso 1 1 calc R U . . .
C15 C 0.22598(18) 0.67471(7) 0.79059(15) 0.0480(4) Uani 1 1 d . . . . .
H15A H 0.1315 0.7039 0.7651 0.058 Uiso 1 1 calc R U . . .
H15B H 0.2723 0.6662 0.7071 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3449(2) 0.71221(9) 0.89756(18) 0.0596(5) Uani 1 1 d . . . . .
H16A H 0.4434 0.6851 0.9149 0.071 Uiso 1 1 calc R U . . .
H16B H 0.3691 0.7579 0.8611 0.071 Uiso 1 1 calc R U . . .
C17 C 0.2482(2) 0.65535(9) 1.08057(18) 0.0640(5) Uani 1 1 d . . . . .
H17A H 0.2078 0.6630 1.1673 0.077 Uiso 1 1 calc R U . . .
H17B H 0.3445 0.6269 1.1014 0.077 Uiso 1 1 calc R U . . .
C18 C 0.12568(19) 0.61635(8) 0.98038(16) 0.0540(4) Uani 1 1 d . . . . .
H18A H 0.1068 0.5703 1.0184 0.065 Uiso 1 1 calc R U . . .
H18B H 0.0255 0.6423 0.9665 0.065 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_3
C16 O1 C17 110.52(12) . .
C1 N1 C2 121.33(12) . .
C1 N2 C15 125.67(12) . .
C1 N2 C18 121.70(12) . .
C15 N2 C18 112.57(11) . .
N1 C1 N2 118.54(13) . .
N1 C1 C8 124.60(12) . .
N2 C1 C8 116.85(11) . .
C3 C2 C7 118.04(14) . .
C3 C2 N1 119.53(13) . .
C7 C2 N1 122.24(13) . .
C4 C3 C2 120.94(15) . .
C5 C4 C3 120.37(16) . .
C6 C5 C4 119.45(16) . .
C5 C6 C7 120.57(15) . .
C6 C7 C2 120.59(15) . .
C9 C8 C1 115.03(11) . .
C10 C9 C14 118.01(13) . .
C10 C9 C8 119.89(12) . .
C14 C9 C8 122.08(12) . .
C9 C10 C11 120.77(14) . .
C12 C11 C10 120.29(15) . .
C13 C12 C11 119.82(15) . .
C12 C13 C14 119.92(16) . .
C9 C14 C13 121.18(15) . .
N2 C15 C16 109.67(12) . .
O1 C16 C15 111.92(13) . .
O1 C17 C18 111.66(14) . .
N2 C18 C17 109.72(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C16 1.418(2) .
O1 C17 1.426(2) .
N1 C1 1.2846(17) .
N1 C2 1.4069(18) .
N2 C1 1.3611(17) .
N2 C15 1.4530(18) .
N2 C18 1.4541(19) .
C1 C8 1.5088(19) .
C2 C3 1.386(2) .
C2 C7 1.388(2) .
C3 C4 1.380(2) .
C4 C5 1.372(3) .
C5 C6 1.371(3) .
C6 C7 1.383(2) .
C8 C9 1.506(2) .
C9 C10 1.3830(19) .
C9 C14 1.383(2) .
C10 C11 1.385(2) .
C11 C12 1.369(3) .
C12 C13 1.370(3) .
C13 C14 1.384(2) .
C15 C16 1.499(2) .
C17 C18 1.494(2) .
