#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153795.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_7153795
loop_
_publ_author_name
'Chen, Jianbin'
'Natte, Kishore'
'Spannenberg, Anke'
'Neumann, Helfried'
'Beller, Matthias'
'Wu, Xiao-Feng'
_publ_section_title
;
 Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes:
 synthesis of thalidomide.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5578
_journal_page_last               5581
_journal_paper_doi               10.1039/c4ob00796d
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.290(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9282(5)
_cell_length_b                   13.3172(6)
_cell_length_c                   6.6540(3)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      3.06
_cell_volume                     1119.35(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15678
_diffrn_reflns_theta_full        28.85
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0432
_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)+(0.0544P)²+0.4257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2185
_reflns_number_total             2926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00796d2.cif
_cod_data_source_block           ax0508
_cod_depositor_comments          'Adding full bibliography for 7153795.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153795
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
C1 C 0.85857(10) 0.32184(10) 0.2509(2) 0.0238(3) Uani 1 1 d .
C2 C 0.96602(10) 0.36642(10) 0.2822(2) 0.0215(3) Uani 1 1 d .
C3 C 1.06412(11) 0.32212(11) 0.3476(2) 0.0247(3) Uani 1 1 d .
H3 H 1.0703 0.2523 0.3772 0.030 Uiso 1 1 calc R
C4 C 1.15407(10) 0.38310(11) 0.3691(2) 0.0246(3) Uani 1 1 d .
C5 C 1.14235(11) 0.48571(11) 0.3246(2) 0.0256(3) Uani 1 1 d .
H5 H 1.2038 0.5264 0.3395 0.031 Uiso 1 1 calc R
C6 C 1.04336(11) 0.52984(11) 0.2593(2) 0.0239(3) Uani 1 1 d .
H6 H 1.0362 0.5996 0.2297 0.029 Uiso 1 1 calc R
C7 C 0.95581(10) 0.46818(10) 0.2393(2) 0.0214(3) Uani 1 1 d .
C8 C 0.84158(11) 0.49290(10) 0.1766(2) 0.0225(3) Uani 1 1 d .
C9 C 1.26245(11) 0.33920(12) 0.4413(3) 0.0338(4) Uani 1 1 d .
H9A H 1.3001 0.3398 0.3280 0.051 Uiso 1 1 calc R
H9B H 1.2562 0.2699 0.4870 0.051 Uiso 1 1 calc R
H9C H 1.3019 0.3792 0.5559 0.051 Uiso 1 1 calc R
C10 C 0.67539(10) 0.39133(10) 0.1434(2) 0.0255(3) Uani 1 1 d .
C11 C 0.62594(12) 0.34693(12) -0.0383(3) 0.0365(4) Uani 1 1 d .
H11 H 0.6652 0.3218 -0.1331 0.044 Uiso 1 1 calc R
C12 C 0.51616(12) 0.34029(13) -0.0776(3) 0.0412(4) Uani 1 1 d .
H12 H 0.4784 0.3102 -0.2010 0.049 Uiso 1 1 calc R
C13 C 0.46304(12) 0.37771(11) 0.0641(3) 0.0356(4) Uani 1 1 d .
H13 H 0.3880 0.3748 0.0401 0.043 Uiso 1 1 calc R
C14 C 0.52098(13) 0.41944(13) 0.2412(3) 0.0377(4) Uani 1 1 d .
H14 H 0.4837 0.4445 0.3392 0.045 Uiso 1 1 calc R
N1 N 0.78831(9) 0.40164(9) 0.18829(19) 0.0245(3) Uani 1 1 d .
N2 N 0.62703(10) 0.42713(10) 0.2847(2) 0.0326(3) Uani 1 1 d .
O1 O 0.83238(8) 0.23629(7) 0.27412(19) 0.0316(3) Uani 1 1 d .
O2 O 0.79899(8) 0.57216(7) 0.12404(16) 0.0284(3) Uani 1 1 d .
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
O1 C1 N1 124.84(12)
O1 C1 C2 129.71(13)
N1 C1 C2 105.44(11)
C3 C2 C7 121.54(12)
C3 C2 C1 129.95(13)
C7 C2 C1 108.49(11)
C2 C3 C4 118.09(13)
C2 C3 H3 121.0
C4 C3 H3 121.0
C5 C4 C3 119.63(12)
C5 C4 C9 120.00(13)
C3 C4 C9 120.36(13)
C6 C5 C4 121.98(13)
C6 C5 H5 119.0
C4 C5 H5 119.0
C7 C6 C5 117.34(13)
C7 C6 H6 121.3
C5 C6 H6 121.3
C6 C7 C2 121.42(12)
C6 C7 C8 129.89(13)
C2 C7 C8 108.68(11)
O2 C8 N1 124.94(12)
O2 C8 C7 129.84(13)
N1 C8 C7 105.22(11)
C4 C9 H9A 109.5
C4 C9 H9B 109.5
H9A C9 H9B 109.5
C4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C11 125.31(14)
N2 C10 N1 115.57(13)
C11 C10 N1 119.13(14)
C10 C11 C12 117.24(16)
C10 C11 H11 121.4
C12 C11 H11 121.4
C13 C12 C11 119.19(16)
C13 C12 H12 120.4
C11 C12 H12 120.4
C14 C13 C12 118.38(14)
C14 C13 H13 120.8
C12 C13 H13 120.8
N2 C14 C13 124.16(16)
N2 C14 H14 117.9
C13 C14 H14 117.9
C1 N1 C8 112.16(11)
C1 N1 C10 123.78(11)
C8 N1 C10 124.06(11)
C10 N2 C14 115.72(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2078(17)
C1 N1 1.4025(17)
C1 C2 1.4840(18)
C2 C3 1.3824(18)
C2 C7 1.3855(19)
C3 C4 1.4005(19)
C3 H3 0.9500
C4 C5 1.399(2)
C4 C9 1.4998(19)
C5 C6 1.3911(19)
C5 H5 0.9500
C6 C7 1.3817(19)
C6 H6 0.9500
C7 C8 1.4835(18)
C8 O2 1.2075(16)
C8 N1 1.4072(17)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 N2 1.324(2)
C10 C11 1.375(2)
C10 N1 1.4330(17)
C11 C12 1.390(2)
C11 H11 0.9500
C12 C13 1.373(3)
C12 H12 0.9500
C13 C14 1.372(2)
C13 H13 0.9500
C14 N2 1.344(2)
C14 H14 0.9500
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
O1 C1 C2 C3 -0.6(3)
N1 C1 C2 C3 178.62(14)
O1 C1 C2 C7 -178.92(16)
N1 C1 C2 C7 0.32(16)
C7 C2 C3 C4 -0.2(2)
C1 C2 C3 C4 -178.35(14)
C2 C3 C4 C5 0.1(2)
C2 C3 C4 C9 179.46(13)
C3 C4 C5 C6 0.1(2)
C9 C4 C5 C6 -179.32(14)
C4 C5 C6 C7 -0.1(2)
C5 C6 C7 C2 -0.1(2)
C5 C6 C7 C8 179.07(14)
C3 C2 C7 C6 0.2(2)
C1 C2 C7 C6 178.71(13)
C3 C2 C7 C8 -179.08(13)
C1 C2 C7 C8 -0.60(15)
C6 C7 C8 O2 2.0(3)
C2 C7 C8 O2 -178.80(15)
C6 C7 C8 N1 -178.58(14)
C2 C7 C8 N1 0.65(15)
N2 C10 C11 C12 0.8(3)
N1 C10 C11 C12 -178.73(14)
C10 C11 C12 C13 0.0(3)
C11 C12 C13 C14 -0.7(3)
C12 C13 C14 N2 0.7(3)
O1 C1 N1 C8 179.40(15)
C2 C1 N1 C8 0.11(16)
O1 C1 N1 C10 0.0(2)
C2 C1 N1 C10 -179.33(13)
O2 C8 N1 C1 179.02(14)
C7 C8 N1 C1 -0.46(16)
O2 C8 N1 C10 -1.5(2)
C7 C8 N1 C10 178.97(13)
N2 C10 N1 C1 105.13(16)
C11 C10 N1 C1 -75.3(2)
N2 C10 N1 C8 -74.24(18)
C11 C10 N1 C8 105.35(17)
C11 C10 N2 C14 -0.9(2)
N1 C10 N2 C14 178.69(13)
C13 C14 N2 C10 0.1(2)
