#------------------------------------------------------------------------------
#$Date: 2015-09-06 02:43:07 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154690 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/13/4031320.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_4031320
loop_
_publ_author_name
'Xuan, Zi'
'Kim, Ju Hyun'
'Lee, Sang-Gi'
_publ_section_title
;
 Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot
 Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7824
_journal_page_last               7829
_journal_paper_doi               10.1021/acs.joc.5b01375
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C22 H21 N O4'
_chemical_formula_weight         363.40
_chemical_name_common            SKL-20150302
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 107.5360(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4913(4)
_cell_length_b                   8.9886(2)
_cell_length_c                   15.3931(4)
_cell_measurement_reflns_used    9238
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.1407
_cell_measurement_theta_min      2.7033
_cell_volume                     1911.87(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28426
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0498
_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)+(0.0601P)²+1.4085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                1888
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b01375_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4031319--4031320.cif.'
_cod_database_code               4031320
loop_
_space_group_symop_operation_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_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.05346(10) 0.38728(14) 0.26801(9) 0.0351(3) Uani d . . . 1
C C2 0.10381(13) 0.51679(17) 0.25922(11) 0.0480(4) Uani d . . . 1
H H2 0.0695 0.5988 0.2293 0.058 Uiso calc U . R 1
C C3 0.20314(14) 0.5251(2) 0.29405(12) 0.0584(5) Uani d . . . 1
H H3 0.235 0.6122 0.2874 0.07 Uiso calc U . R 1
C C4 0.25523(13) 0.4053(2) 0.33857(12) 0.0563(5) Uani d . . . 1
H H4 0.3223 0.4107 0.3617 0.068 Uiso calc U . R 1
C C5 0.20732(11) 0.27663(18) 0.34867(11) 0.0459(4) Uani d . . . 1
H H5 0.2427 0.196 0.3792 0.055 Uiso calc U . R 1
C C6 0.10663(10) 0.26526(14) 0.31384(9) 0.0344(3) Uani d . . . 1
C C7 0.06284(10) 0.11967(14) 0.32577(9) 0.0344(3) Uani d . . . 1
C C8 0.09409(11) 0.04588(15) 0.40568(10) 0.0395(3) Uani d . . . 1
H H8 0.1394 0.0928 0.4538 0.047 Uiso calc U . R 1
C C9 0.06179(11) -0.10214(16) 0.42170(11) 0.0428(4) Uani d . . . 1
C C10 0.07707(15) -0.2885(2) 0.53565(16) 0.0658(5) Uani d . . . 1
H H10A 0.0128 -0.3163 0.4979 0.079 Uiso calc U . R 1
H H10B 0.0764 -0.2857 0.5985 0.079 Uiso calc U . R 1
C C11 0.1461(2) -0.3997(3) 0.5265(2) 0.0951(9) Uani d . . . 1
H H11A 0.1448 -0.4061 0.4639 0.143 Uiso calc U . R 1
H H11B 0.1293 -0.4946 0.5461 0.143 Uiso calc U . R 1
H H11C 0.2099 -0.3722 0.5634 0.143 Uiso calc U . R 1
N N1 0 0.05396(19) 0.25 0.0472(5) Uani d T P S 1
H H1N 0 -0.042(4) 0.25 0.071 Uiso d U P S 1
O O1 0.00712(10) -0.18057(13) 0.36579(9) 0.0661(4) Uani d . . . 1
O O2 0.10027(9) -0.14220(13) 0.50928(8) 0.0572(3) 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_site_symmetry_3
_geom_angle
C2 C1 C6 . 118.36(13)
C2 C1 C1 2 118.71(10)
C6 C1 C1 2 122.88(9)
C3 C2 C1 . 121.35(15)
C4 C3 C2 . 120.26(15)
C3 C4 C5 . 119.55(16)
C4 C5 C6 . 121.32(15)
C5 C6 C1 . 119.17(13)
C5 C6 C7 . 116.81(12)
C1 C6 C7 . 124.00(12)
C8 C7 N1 . 121.02(13)
C8 C7 C6 . 120.36(12)
N1 C7 C6 . 118.02(12)
C7 C8 C9 . 124.52(13)
O1 C9 O2 . 122.97(14)
O1 C9 C8 . 126.08(14)
O2 C9 C8 . 110.95(13)
O2 C10 C11 . 111.97(17)
C7 N1 C7 2 129.24(17)
C9 O2 C10 . 117.67(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.4019(19)
C1 C6 . 1.4025(19)
C1 C1 2 1.480(3)
C2 C3 . 1.378(3)
C3 C4 . 1.374(3)
C4 C5 . 1.381(2)
C5 C6 . 1.398(2)
C6 C7 . 1.4897(18)
C7 C8 . 1.3500(19)
C7 N1 . 1.3778(15)
C8 C9 . 1.456(2)
C9 O1 . 1.2060(19)
C9 O2 . 1.3435(18)
C10 O2 . 1.445(2)
C10 C11 . 1.451(3)
N1 C7 2 1.3778(15)
