#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:57:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178452 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/73/4027326.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_4027326
loop_
_publ_author_name
'Dennis U. Nielsen'
'Karoline Neumann'
'Rolf H. Taaning'
'Anders T. Lindhardt'
'Amalie Modvig'
'Troels Skrydstrup'
_publ_contact_author_address
;
Department of Chemistry
Aarhus University
Langelandsgade 140
DK-8000 Aarhus C
;
_publ_contact_author_email       jacobo@chem.au.dk
_publ_contact_author_fax         '+45 8619 6199'
_publ_contact_author_name        'Overgaard, Jacob'
_publ_contact_author_phone       '+45 8942 3891'
_publ_section_title
;
 Palladium-Catalyzed Double Carbonylation Using Near Stoichiometric Carbon
 Monoxide: Expedient Access to Substituted 13C2-Labeled Phenethylamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6155
_journal_page_last               6165
_journal_paper_doi               10.1021/jo3009337
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.28
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2011-11-17
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.066(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3286(3)
_cell_length_b                   10.3522(2)
_cell_length_c                   10.2050(2)
_cell_measurement_reflns_used    9276
_cell_measurement_temperature    250.01(11)
_cell_measurement_theta_max      28.6041
_cell_measurement_theta_min      1.6577
_cell_volume                     1295.15(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      250.01(11)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
  1 omega  -70.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337  -19.0000    0.0000 181

  2 omega   35.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  178.0000  150.0000 33

  3 omega  -75.00  113.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337   19.0000  150.0000 188

  4 omega   34.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337 -178.0000  120.0000 84

  5 omega  -20.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  -99.0000  -90.0000 51

  6 omega  -20.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  -99.0000 -150.0000 51

  7 omega   35.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  178.0000  -30.0000 46

  8 omega  -61.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931   57.0000  -90.0000 133

  9 omega  -28.00   39.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337   38.0000  -90.0000 67

 10 omega   34.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337 -178.0000  -90.0000 84
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_UB_11      0.0084886000
_diffrn_orient_matrix_UB_12      0.0042135000
_diffrn_orient_matrix_UB_13      -0.0675378000
_diffrn_orient_matrix_UB_21      -0.0495866000
_diffrn_orient_matrix_UB_22      0.0346630000
_diffrn_orient_matrix_UB_23      -0.0129761000
_diffrn_orient_matrix_UB_31      0.0285076000
_diffrn_orient_matrix_UB_32      0.0590115000
_diffrn_orient_matrix_UB_33      0.0123638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20601
_diffrn_reflns_theta_full        28.67
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_min         1.66
_diffrn_source                   ' 'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.4293
_exptl_crystal_size_min          0.3241
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0414
_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)+(0.0447P)²+0.1986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2453
_reflns_number_total             3161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3009337_si_002.cif
_cod_data_source_block           11jo0022s
_cod_original_cell_volume        1295.16(5)
_cod_database_code               4027326
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C13 H17 N O3'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
N1 N 0.34410(8) 0.20581(9) 0.23111(8) 0.0414(2) Uani 1 1 d .
H1 H 0.3245 0.2183 0.1487 0.050 Uiso 1 1 calc R
O2 O 0.31494(7) 0.26987(10) 0.43765(7) 0.0568(3) Uani 1 1 d .
C3 C 0.29356(9) 0.27330(11) 0.31734(11) 0.0429(3) Uani 1 1 d .
C4 C 0.09800(10) 0.36117(11) 0.31507(11) 0.0453(3) Uani 1 1 d .
C5 C 0.20230(11) 0.36234(12) 0.25661(11) 0.0487(3) Uani 1 1 d .
C6 C 0.43186(9) 0.11042(10) 0.26721(10) 0.0398(3) Uani 1 1 d .
C7 C 0.07271(10) 0.26813(12) 0.40515(12) 0.0495(3) Uani 1 1 d .
H7 H 0.1237 0.2045 0.4314 0.059 Uiso 1 1 calc R
O8 O 0.21991(9) 0.43208(11) 0.16515(10) 0.0759(3) Uani 1 1 d .
O9 O -0.20075(8) 0.37528(11) 0.46652(12) 0.0772(3) Uani 1 1 d .
C10 C -0.10194(10) 0.36411(13) 0.41979(14) 0.0556(3) Uani 1 1 d .
C11 C 0.38910(11) 0.00443(12) 0.35202(12) 0.0524(3) Uani 1 1 d .
H11A H 0.3670 0.0418 0.4311 0.079 Uiso 1 1 calc R
H11B H 0.4457 -0.0579 0.3745 0.079 Uiso 1 1 calc R
H11C H 0.3278 -0.0373 0.3038 0.079 Uiso 1 1 calc R
C12 C -0.02670(11) 0.26804(13) 0.45665(14) 0.0544(3) Uani 1 1 d .
H12 H -0.0428 0.2040 0.5155 0.065 Uiso 1 1 calc R
C13 C 0.46174(12) 0.05163(13) 0.13944(12) 0.0536(3) Uani 1 1 d .
H13A H 0.3984 0.0119 0.0934 0.080 Uiso 1 1 calc R
H13B H 0.5176 -0.0123 0.1588 0.080 Uiso 1 1 calc R
H13C H 0.4881 0.1181 0.0854 0.080 Uiso 1 1 calc R
C14 C 0.53126(10) 0.17657(12) 0.33885(12) 0.0513(3) Uani 1 1 d .
H14A H 0.5553 0.2444 0.2846 0.077 Uiso 1 1 calc R
H14B H 0.5888 0.1146 0.3570 0.077 Uiso 1 1 calc R
H14C H 0.5124 0.2125 0.4202 0.077 Uiso 1 1 calc R
C15 C -0.07809(11) 0.45800(13) 0.32987(15) 0.0605(4) Uani 1 1 d .
H15 H -0.1287 0.5224 0.3050 0.073 Uiso 1 1 calc R
C16 C 0.02002(11) 0.45595(12) 0.27774(13) 0.0543(3) Uani 1 1 d .
H16 H 0.0349 0.5185 0.2167 0.065 Uiso 1 1 calc R
C2 C -0.22717(14) 0.2853(2) 0.5637(2) 0.0939(6) Uani 1 1 d .
H2A H -0.2270 0.1995 0.5282 0.141 Uiso 1 1 calc R
H2B H -0.2982 0.3047 0.5890 0.141 Uiso 1 1 calc R
H2C H -0.1741 0.2912 0.6394 0.141 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3 13 -7 0.1408 3.0000 13.0000 -7.0000 0.5530 0.3927 0.7661
-6 -13 3 0.2245 -6.0000 -13.0000 3.0000 -0.3083 -0.1920 -0.9011
6 1 13 0.1466 6.0000 1.0000 13.0000 -0.8228 -0.4315 0.3908
-7 -3 -12 0.1546 -7.0000 -3.0000 -12.0000 0.7384 0.3988 -0.5250
-16 6 1 0.1700 -16.0000 6.0000 1.0000 -0.1781 0.9884 -0.0897
17 -3 -1 0.1825 17.0000 -3.0000 -1.0000 0.1992 -0.9340 0.2952
12 -10 -2 0.1876 12.0000 -10.0000 -2.0000 0.1948 -0.9157 -0.2728
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N1 H1 117.7
C3 N1 C6 124.51(9)
C6 N1 H1 117.7
N1 C3 C5 115.06(9)
O2 C3 N1 125.47(11)
O2 C3 C5 119.46(10)
C7 C4 C5 122.68(11)
C7 C4 C16 118.09(12)
C16 C4 C5 119.23(11)
C4 C5 C3 117.76(10)
O8 C5 C3 118.91(11)
O8 C5 C4 123.30(11)
N1 C6 C11 109.46(9)
N1 C6 C13 106.88(9)
N1 C6 C14 110.43(9)
C13 C6 C11 109.18(10)
C13 C6 C14 109.67(10)
C14 C6 C11 111.11(9)
C4 C7 H7 119.3
C12 C7 C4 121.43(11)
C12 C7 H7 119.3
C10 O9 C2 117.93(12)
O9 C10 C12 124.43(13)
O9 C10 C15 115.61(12)
C12 C10 C15 119.96(12)
C6 C11 H11A 109.5
C6 C11 H11B 109.5
C6 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C7 C12 C10 119.43(12)
C7 C12 H12 120.3
C10 C12 H12 120.3
C6 C13 H13A 109.5
C6 C13 H13B 109.5
C6 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C6 C14 H14A 109.5
C6 C14 H14B 109.5
C6 C14 H14C 109.5
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C10 C15 H15 119.9
C16 C15 C10 120.13(12)
C16 C15 H15 119.9
C4 C16 H16 119.5
C15 C16 C4 120.95(12)
C15 C16 H16 119.5
O9 C2 H2A 109.5
O9 C2 H2B 109.5
O9 C2 H2C 109.5
H2A C2 H2B 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 H1 0.8600
N1 C3 1.3291(14)
N1 C6 1.4823(14)
O2 C3 1.2288(13)
C3 C5 1.5337(17)
C4 C5 1.4736(17)
C4 C7 1.3895(17)
C4 C16 1.3981(16)
C5 O8 1.2175(14)
C6 C11 1.5256(15)
C6 C13 1.5191(15)
C6 C14 1.5218(16)
C7 H7 0.9300
C7 C12 1.3836(18)
O9 C10 1.3592(16)
O9 C2 1.423(2)
C10 C12 1.3846(18)
C10 C15 1.3894(19)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15 0.9300
C15 C16 1.3720(19)
C16 H16 0.9300
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
