#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029231.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_4029231
loop_
_publ_author_name
'Mancuso, Raffaella'
'Ziccarelli, Ida'
'Armentano, Donatella'
'Marino, Nadia'
'Giofrè, Salvatore V'
'Gabriele, Bartolo'
_publ_section_title
;
 Divergent palladium iodide catalyzed multicomponent carbonylative
 approaches to functionalized isoindolinone and isobenzofuranimine
 derivatives.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3506
_journal_page_last               3518
_journal_paper_doi               10.1021/jo500281h
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C18 H22 N2 O3'
_chemical_formula_weight         314.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.151(5)
_cell_length_b                   10.361(7)
_cell_length_c                   18.314(15)
_cell_measurement_reflns_used    3111
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.5
_cell_measurement_theta_min      2.2
_cell_volume                     1736(2)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8135
_diffrn_reflns_theta_full        18.64
_diffrn_reflns_theta_max         18.64
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.102
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.3492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                1217
_reflns_number_total             1308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500281h_si_002.cif
_cod_data_source_block           bg_2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029231.cif.
;
_cod_original_cell_volume        1737(2)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4029231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
O1 O 0.1397(3) 0.6749(3) -0.03875(17) 0.0764(10) Uani 1 1 d .
O2 O -0.1893(4) 0.3108(2) -0.0077(2) 0.0900(10) Uani 1 1 d .
O3 O 0.2141(3) 0.9466(3) 0.2743(2) 0.0862(11) Uani 1 1 d .
N1 N -0.0563(4) 0.5558(3) -0.00514(18) 0.0629(10) Uani 1 1 d .
N2 N 0.0861(3) 0.8847(3) 0.1685(2) 0.0471(9) Uani 1 1 d .
C1 C 0.0371(5) 0.6564(4) 0.0036(3) 0.0558(11) Uani 1 1 d .
C2 C 0.0040(4) 0.7473(3) 0.0651(2) 0.0507(11) Uani 1 1 d .
H2 H -0.0901 0.7807 0.0683 0.061 Uiso 1 1 calc R
C3 C 0.1011(4) 0.7834(3) 0.1156(2) 0.0438(10) Uani 1 1 d .
C4 C 0.2410(4) 0.7181(4) 0.1323(3) 0.0511(11) Uani 1 1 d .
C5 C 0.3124(5) 0.6112(4) 0.1019(3) 0.0754(14) Uani 1 1 d .
H5 H 0.2758 0.5687 0.0611 0.090 Uiso 1 1 calc R
C6 C 0.4406(7) 0.5721(5) 0.1358(4) 0.1012(18) Uani 1 1 d .
H6 H 0.4892 0.5009 0.1167 0.121 Uiso 1 1 calc R
C7 C 0.5009(6) 0.6319(7) 0.1962(4) 0.109(2) Uani 1 1 d .
H7 H 0.5879 0.6023 0.2164 0.130 Uiso 1 1 calc R
C8 C 0.4288(6) 0.7369(6) 0.2258(3) 0.0904(16) Uani 1 1 d .
H8 H 0.4660 0.7796 0.2664 0.108 Uiso 1 1 calc R
C9 C 0.2987(4) 0.7771(4) 0.1931(3) 0.0607(12) Uani 1 1 d .
C10 C 0.1994(4) 0.8810(4) 0.2195(3) 0.0545(11) Uani 1 1 d .
C11 C -0.0463(6) 0.4736(4) -0.0712(3) 0.0842(15) Uani 1 1 d .
H11A H 0.0473 0.4866 -0.0950 0.101 Uiso 1 1 calc R
H11B H -0.1229 0.4967 -0.1054 0.101 Uiso 1 1 calc R
C12 C -0.0621(7) 0.3359(4) -0.0494(3) 0.0981(17) Uani 1 1 d .
H12A H -0.0643 0.2829 -0.0930 0.118 Uiso 1 1 calc R
H12B H 0.0229 0.3107 -0.0211 0.118 Uiso 1 1 calc R
C13 C -0.1865(6) 0.3864(4) 0.0577(3) 0.0846(14) Uani 1 1 d .
H13A H -0.1015 0.3629 0.0863 0.102 Uiso 1 1 calc R
H13B H -0.2728 0.3673 0.0865 0.102 Uiso 1 1 calc R
C14 C -0.1821(5) 0.5249(4) 0.0418(3) 0.0765(14) Uani 1 1 d .
H14A H -0.1747 0.5729 0.0872 0.092 Uiso 1 1 calc R
H14B H -0.2718 0.5505 0.0176 0.092 Uiso 1 1 calc R
C15 C -0.0366(4) 0.9811(3) 0.1704(3) 0.0600(12) Uani 1 1 d .
C16 C -0.1726(5) 0.9153(5) 0.2009(3) 0.113(2) Uani 1 1 d .
H16A H -0.1535 0.8864 0.2498 0.169 Uiso 1 1 calc R
H16B H -0.1974 0.8427 0.1709 0.169 Uiso 1 1 calc R
H16C H -0.2524 0.9755 0.2013 0.169 Uiso 1 1 calc R
C17 C -0.0658(5) 1.0340(4) 0.0937(3) 0.0856(16) Uani 1 1 d .
H17A H -0.0997 0.9654 0.0628 0.128 Uiso 1 1 calc R
H17B H 0.0228 1.0693 0.0740 0.128 Uiso 1 1 calc R
H17C H -0.1388 1.1003 0.0962 0.128 Uiso 1 1 calc R
C18 C 0.0064(7) 1.0994(5) 0.2157(3) 0.145(3) Uani 1 1 d .
H18A H 0.1047 1.1242 0.2040 0.217 Uiso 1 1 calc R
H18B H 0.0001 1.0788 0.2667 0.217 Uiso 1 1 calc R
H18C H -0.0587 1.1695 0.2048 0.217 Uiso 1 1 calc 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O2 C13 109.6(3)
C1 N1 C14 126.1(4)
C1 N1 C11 119.9(4)
C14 N1 C11 113.6(3)
C10 N2 C3 111.1(3)
C10 N2 C15 123.9(3)
C3 N2 C15 125.0(3)
O1 C1 N1 121.6(4)
O1 C1 C2 122.0(4)
N1 C1 C2 116.3(4)
C3 C2 C1 124.1(3)
C2 C3 N2 127.4(3)
C2 C3 C4 126.3(4)
N2 C3 C4 106.1(3)
C9 C4 C5 119.6(4)
C9 C4 C3 107.3(4)
C5 C4 C3 133.0(5)
C6 C5 C4 116.6(5)
C7 C6 C5 124.4(5)
C8 C7 C6 118.4(5)
C7 C8 C9 118.2(5)
C4 C9 C8 122.8(5)
C4 C9 C10 110.4(4)
C8 C9 C10 126.6(6)
O3 C10 N2 128.1(4)
O3 C10 C9 127.0(4)
N2 C10 C9 104.8(4)
N1 C11 C12 109.0(4)
O2 C12 C11 113.6(4)
O2 C13 C14 111.8(4)
C13 C14 N1 110.5(4)
N2 C15 C16 108.7(3)
N2 C15 C17 110.3(3)
C16 C15 C17 110.7(4)
N2 C15 C18 110.7(3)
C16 C15 C18 111.6(5)
C17 C15 C18 104.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.232(5)
O2 C12 1.415(6)
O2 C13 1.432(5)
O3 C10 1.219(5)
N1 C1 1.358(5)
N1 C14 1.472(5)
N1 C11 1.483(5)
N2 C10 1.395(5)
N2 C3 1.436(5)
N2 C15 1.503(5)
C1 C2 1.499(5)
C2 C3 1.337(5)
C3 C4 1.480(5)
C4 C9 1.375(5)
C4 C5 1.401(5)
C5 C6 1.388(7)
C6 C7 1.382(7)
C7 C8 1.383(7)
C8 C9 1.397(6)
C9 C10 1.490(6)
C11 C12 1.489(6)
C13 C14 1.465(5)
C15 C16 1.525(6)
C15 C17 1.531(6)
C15 C18 1.532(6)
