#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029230.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_4029230
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            'C15 H17 N O3'
_chemical_formula_weight         259.30
_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                 106.251(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6562(12)
_cell_length_b                   9.0022(8)
_cell_length_c                   12.1433(10)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.7
_cell_volume                     1433.2(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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29631
_diffrn_reflns_theta_full        26.78
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.988
_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       parallelepiped
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0392
_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)+(0.0721P)²+0.1654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                2444
_reflns_number_total             3042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500281h_si_004.cif
_cod_data_source_block           bg_8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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/4029230.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/C
_cod_database_code               4029230
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
O1 O 1.08440(8) -0.17021(14) 0.38407(12) 0.0821(4) Uani 1 1 d .
O2 O 0.78261(6) 0.02989(10) 0.34445(8) 0.0483(3) Uani 1 1 d .
O3 O 1.09906(7) 0.03232(14) 0.28178(9) 0.0666(3) Uani 1 1 d .
N1 N 0.62054(8) -0.00518(12) 0.37833(10) 0.0489(3) Uani 1 1 d .
C1 C 1.04859(10) -0.05610(17) 0.33762(12) 0.0534(3) Uani 1 1 d .
C2 C 0.94837(9) 0.00965(16) 0.33003(11) 0.0495(3) Uani 1 1 d .
H2 H 0.9348 0.1017 0.2943 0.059 Uiso 1 1 calc R
C3 C 0.87435(9) -0.04977(14) 0.36950(10) 0.0443(3) Uani 1 1 d .
C4 C 0.86109(9) -0.18408(14) 0.43351(10) 0.0446(3) Uani 1 1 d .
C5 C 0.92773(11) -0.29791(15) 0.48694(11) 0.0538(3) Uani 1 1 d .
H5 H 0.9953 -0.2991 0.4848 0.065 Uiso 1 1 calc R
C6 C 0.88974(12) -0.40827(17) 0.54290(12) 0.0596(4) Uani 1 1 d .
H6 H 0.9329 -0.4845 0.5788 0.072 Uiso 1 1 calc R
C7 C 0.78874(12) -0.40882(17) 0.54710(13) 0.0610(4) Uani 1 1 d .
H7 H 0.7655 -0.4856 0.5844 0.073 Uiso 1 1 calc R
C8 C 0.72244(11) -0.29530(16) 0.49584(12) 0.0556(4) Uani 1 1 d .
H8 H 0.6551 -0.2941 0.4986 0.067 Uiso 1 1 calc R
C9 C 0.76066(9) -0.18365(14) 0.44024(11) 0.0456(3) Uani 1 1 d .
C10 C 0.71009(9) -0.04747(14) 0.38534(11) 0.0441(3) Uani 1 1 d .
C11 C 1.19845(12) -0.0194(2) 0.27847(17) 0.0823(6) Uani 1 1 d .
H11A H 1.2414 -0.0319 0.3553 0.123 Uiso 1 1 calc R
H11B H 1.2285 0.0522 0.2391 0.123 Uiso 1 1 calc R
H11C H 1.1915 -0.1127 0.2388 0.123 Uiso 1 1 calc R
C12 C 0.57798(10) 0.14056(15) 0.32938(12) 0.0509(3) Uani 1 1 d .
C14 C 0.57999(12) 0.15785(19) 0.20450(13) 0.0648(4) Uani 1 1 d .
H14A H 0.6493 0.1672 0.2018 0.097 Uiso 1 1 calc R
H14B H 0.5424 0.2451 0.1721 0.097 Uiso 1 1 calc R
H14C H 0.5495 0.0721 0.1614 0.097 Uiso 1 1 calc R
C13 C 0.63808(13) 0.26628(18) 0.40435(14) 0.0698(4) Uani 1 1 d .
H13A H 0.6358 0.2533 0.4821 0.105 Uiso 1 1 calc R
H13B H 0.6083 0.3602 0.3760 0.105 Uiso 1 1 calc R
H13C H 0.7077 0.2638 0.4018 0.105 Uiso 1 1 calc R
C15 C 0.46692(12) 0.1411(2) 0.33433(17) 0.0765(5) Uani 1 1 d .
H15A H 0.4302 0.0619 0.2877 0.115 Uiso 1 1 calc R
H15B H 0.4358 0.2344 0.3062 0.115 Uiso 1 1 calc R
H15C H 0.4653 0.1273 0.4122 0.115 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'
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
C3 O2 C10 110.14(10)
C1 O3 C11 116.01(13)
C10 N1 C12 123.75(11)
O1 C1 O3 122.55(12)
O1 C1 C2 128.32(13)
O3 C1 C2 109.13(13)
C3 C2 C1 126.64(14)
C2 C3 O2 115.76(12)
C2 C3 C4 136.80(12)
O2 C3 C4 107.43(10)
C9 C4 C5 119.71(12)
C9 C4 C3 107.21(10)
C5 C4 C3 133.04(12)
C6 C5 C4 117.87(13)
C5 C6 C7 122.08(13)
C8 C7 C6 120.50(14)
C9 C8 C7 117.53(13)
C8 C9 C4 122.29(12)
C8 C9 C10 129.00(12)
C4 C9 C10 108.65(11)
N1 C10 O2 126.21(12)
N1 C10 C9 127.26(12)
O2 C10 C9 106.51(10)
N1 C12 C14 111.80(11)
N1 C12 C15 105.45(11)
C14 C12 C15 109.28(12)
N1 C12 C13 109.14(11)
C14 C12 C13 110.90(12)
C15 C12 C13 110.13(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2075(18)
O2 C3 1.4011(14)
O2 C10 1.4099(15)
O3 C1 1.3528(18)
O3 C11 1.4460(17)
N1 C10 1.2607(15)
N1 C12 1.4897(16)
C1 C2 1.4701(18)
C2 C3 1.3449(18)
C3 C4 1.4757(18)
C4 C9 1.3966(17)
C4 C5 1.4031(17)
C5 C6 1.384(2)
C6 C7 1.394(2)
C7 C8 1.391(2)
C8 C9 1.3913(19)
C9 C10 1.4719(17)
C12 C14 1.532(2)
C12 C15 1.5346(19)
C12 C13 1.538(2)
