#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:01:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178734 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/45/4084580.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_4084580
loop_
_publ_author_name
'Oliva-Madrid, María-José'
'García-López, José-Antonio'
'Saura-Llamas, Isabel'
'Bautista, Delia'
'Vicente, José'
_publ_section_title
;
 Insertion Reactions on Carbopalladated Benzyne: From Eight- to Nine- and
 Ten-Membered Palladacycles. Applications to the Synthesis of
 N-Heterocycles
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6420
_journal_paper_doi               10.1021/om500772p
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_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                 106.665(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.838(9)
_cell_length_b                   6.389(4)
_cell_length_c                   20.408(13)
_cell_measurement_reflns_used    4793
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.85
_cell_volume                     1853(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21913
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.8326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.015
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
;
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, other riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0665
_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)+(0.1053P)²+0.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1928
_reflns_number_gt                3370
_reflns_number_total             4535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500772p_si_002.cif
_cod_data_source_block           jof251_squeezed
_cod_depositor_comments
'Adding full bibliography for 4084578--4084580.cif.'
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4084580
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 0.29361(14) 0.7516(3) -0.07161(10) 0.0314(4) Uani 1 1 d .
H1 H 0.2674 0.8780 -0.0920 0.038 Uiso 1 1 calc R
C2 C 0.33854(13) 0.6239(3) -0.10643(9) 0.0302(4) Uani 1 1 d .
O2 O 0.34846(11) 0.6655(2) -0.16949(7) 0.0403(4) Uani 1 1 d .
C3 C 0.37937(12) 0.4354(3) -0.07622(9) 0.0283(4) Uani 1 1 d .
O3 O 0.42271(10) 0.3192(2) -0.11448(7) 0.0369(3) Uani 1 1 d .
C4 C 0.36990(13) 0.3800(3) -0.01345(9) 0.0293(4) Uani 1 1 d .
H4 H 0.3960 0.2529 0.0064 0.035 Uiso 1 1 calc R
C5 C 0.32214(12) 0.5080(3) 0.02206(9) 0.0268(4) Uani 1 1 d .
C6 C 0.28537(13) 0.6995(3) -0.00626(9) 0.0288(4) Uani 1 1 d .
C7 C 0.13774(12) 0.4222(3) 0.05134(9) 0.0264(4) Uani 1 1 d .
N1 N 0.11707(12) 0.6239(2) 0.03765(9) 0.0315(4) Uani 1 1 d .
H01 H 0.061(2) 0.654(4) 0.0099(13) 0.044(6) Uiso 1 1 d .
O1 O 0.08166(10) 0.2794(2) 0.02611(7) 0.0355(3) Uani 1 1 d .
C8 C 0.24417(16) 0.8664(3) 0.02899(12) 0.0377(5) Uani 1 1 d .
H8A H 0.2099 0.9657 -0.0059 0.045 Uiso 1 1 calc R
H8B H 0.2964 0.9431 0.0600 0.045 Uiso 1 1 calc R
C9 C 0.17833(14) 0.7959(3) 0.06968(10) 0.0319(4) Uani 1 1 d .
H9A H 0.2159 0.7523 0.1154 0.038 Uiso 1 1 calc R
H9B H 0.1394 0.9149 0.0752 0.038 Uiso 1 1 calc R
C10 C 0.23080(13) 0.3718(3) 0.10109(9) 0.0261(4) Uani 1 1 d .
C12 C 0.2950(2) 0.8330(4) -0.20702(12) 0.0532(6) Uani 1 1 d .
H12A H 0.2289 0.8113 -0.2111 0.080 Uiso 1 1 calc R
H12B H 0.3039 0.8385 -0.2523 0.080 Uiso 1 1 calc R
H12C H 0.3157 0.9638 -0.1833 0.080 Uiso 1 1 calc R
C13 C 0.47852(15) 0.1472(3) -0.08163(12) 0.0406(5) Uani 1 1 d .
H13A H 0.5238 0.1951 -0.0399 0.061 Uiso 1 1 calc R
H13B H 0.5116 0.0879 -0.1120 0.061 Uiso 1 1 calc R
H13C H 0.4383 0.0415 -0.0706 0.061 Uiso 1 1 calc R
C14 C 0.39973(14) 0.3639(3) 0.13795(10) 0.0349(4) Uani 1 1 d .
H14 H 0.4580 0.3969 0.1309 0.042 Uiso 1 1 calc R
C15 C 0.31710(13) 0.4218(3) 0.08915(9) 0.0277(4) Uani 1 1 d .
C16 C 0.23050(16) 0.2637(3) 0.16058(10) 0.0329(4) Uani 1 1 d .
H16 H 0.1728 0.2297 0.1684 0.040 Uiso 1 1 calc R
C17 C 0.31334(17) 0.2063(3) 0.20788(10) 0.0391(5) Uani 1 1 d .
H17 H 0.3121 0.1321 0.2474 0.047 Uiso 1 1 calc R
C18 C 0.39762(17) 0.2580(3) 0.19708(11) 0.0405(5) Uani 1 1 d .
H18 H 0.4543 0.2217 0.2298 0.049 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
C2 C1 C6 122.31(17)
O2 C2 C1 124.93(17)
O2 C2 C3 115.52(16)
C1 C2 C3 119.54(17)
C2 O2 C12 117.51(17)
O3 C3 C4 125.75(17)
O3 C3 C2 115.38(16)
C4 C3 C2 118.82(16)
C3 O3 C13 117.16(15)
C3 C4 C5 122.01(17)
C6 C5 C4 119.33(16)
C6 C5 C15 125.79(16)
C4 C5 C15 114.87(16)
C5 C6 C1 117.88(16)
C5 C6 C8 125.85(17)
C1 C6 C8 116.07(16)
O1 C7 N1 122.37(17)
O1 C7 C10 120.09(16)
N1 C7 C10 117.49(15)
C7 N1 C9 123.92(17)
C6 C8 C9 117.52(16)
N1 C9 C8 113.23(16)
C16 C10 C15 119.49(17)
C16 C10 C7 117.63(17)
C15 C10 C7 122.85(16)
C15 C14 C18 121.07(19)
C14 C15 C10 118.37(17)
C14 C15 C5 119.20(17)
C10 C15 C5 121.90(15)
C17 C16 C10 121.1(2)
C18 C17 C16 119.68(19)
C17 C18 C14 120.33(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.373(3)
C1 C6 1.414(3)
C2 O2 1.363(2)
C2 C3 1.409(3)
O2 C12 1.419(3)
C3 O3 1.365(2)
C3 C4 1.374(3)
O3 C13 1.423(2)
C4 C5 1.411(3)
C5 C6 1.396(3)
C5 C15 1.498(3)
C6 C8 1.510(3)
C7 O1 1.243(2)
C7 N1 1.336(2)
C7 C10 1.496(2)
N1 C9 1.456(2)
C8 C9 1.521(3)
C10 C16 1.398(3)
C10 C15 1.407(3)
C14 C15 1.390(3)
C14 C18 1.392(3)
C16 C17 1.377(3)
C17 C18 1.371(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 O2 0.94 2.50 3.381(3) 155.7 4_566
C9 H9B O1 0.98 2.58 3.414(3) 142.7 1_565
N1 H01 O1 0.88(3) 2.07(3) 2.927(3) 162(2) 3_565
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.051 0.250 258 102 ' '
2 0.000 -0.046 0.750 258 102 ' '
