#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:50:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178980 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/03/4120388.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_4120388
loop_
_publ_author_name
'Jaeyune Ryu'
'Jaesung Kwak'
'Kwangmin Shin'
'Donggun Lee'
'Sukbok Chang'
_publ_section_title
;
 Ir(III)-Catalyzed Mild C-H Amidation of Arenes and Alkenes: An Efficient
 Usage of Acyl Azides as the Nitrogen Source
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12861
_journal_page_last               12868
_journal_paper_doi               10.1021/ja406383h
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C15 H19 N3 O4'
_chemical_formula_sum            'C15 H19 N3 O4'
_chemical_formula_weight         305.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-P 3*'
_symmetry_space_group_name_H-M   'R -3 :R'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                113.28
_cell_angle_beta                 113.28
_cell_angle_gamma                113.28
_cell_formula_units_Z            6
_cell_length_a                   15.5832(8)
_cell_length_b                   15.5832(8)
_cell_length_c                   15.5832(8)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.45
_cell_volume                     2416.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15391
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0520
_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)+(0.1073P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1836
_reflns_number_gt                1766
_reflns_number_total             3184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja406383h_si_002.cif
_cod_data_source_block           No1
_cod_original_cell_volume        2417.2(2)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4120388
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'z, x, y'
'y, z, x'
'-x, -y, -z'
'-z, -x, -y'
'-y, -z, -x'
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 0.11154(17) 0.83728(17) 0.72095(17) 0.0527(5) Uani 1 1 d .
C1 C 0.1364(2) 0.7702(2) 0.7121(2) 0.0399(6) Uani 1 1 d .
C2 C 0.0406(2) 0.6387(2) 0.6502(2) 0.0383(6) Uani 1 1 d .
C3 C -0.0822(2) 0.5836(2) 0.5705(2) 0.0440(6) Uani 1 1 d .
H3 H -0.1025 0.6283 0.5541 0.053 Uiso 1 1 calc R
C4 C -0.1754(2) 0.4645(3) 0.5146(2) 0.0484(7) Uani 1 1 d .
H4 H -0.2596 0.4264 0.4598 0.058 Uiso 1 1 calc R
C5 C -0.1423(2) 0.4026(2) 0.5409(2) 0.0443(7) Uani 1 1 d .
N1 N -0.2394(2) 0.2774(2) 0.4860(2) 0.0574(7) Uani 1 1 d .
O2 O -0.3447(2) 0.2386(2) 0.4327(2) 0.0820(8) Uani 1 1 d .
O3 O -0.2115(2) 0.2168(2) 0.4953(2) 0.0815(7) Uani 1 1 d .
C6 C -0.0216(2) 0.4529(3) 0.6173(2) 0.0459(7) Uani 1 1 d .
H6 H -0.0022 0.4070 0.6320 0.055 Uiso 1 1 calc R
C7 C 0.0703(2) 0.5721(2) 0.6720(2) 0.0442(7) Uani 1 1 d .
H7 H 0.1543 0.6088 0.7247 0.053 Uiso 1 1 calc R
N2 N 0.25109(18) 0.81031(19) 0.75877(19) 0.0430(6) Uani 1 1 d .
H2A H 0.2417 0.7591 0.6933 0.052 Uiso 1 1 d R
C8 C 0.3492(2) 0.9287(2) 0.8185(2) 0.0420(6) Uani 1 1 d .
H8 H 0.3354 0.9850 0.8299 0.050 Uiso 1 1 calc R
C9 C 0.4620(2) 0.9708(2) 0.8617(2) 0.0402(6) Uani 1 1 d .
C10 C 0.5616(3) 1.1030(2) 0.9283(3) 0.0519(7) Uani 1 1 d .
H10A H 0.5314 1.1473 0.9403 0.078 Uiso 1 1 calc R
H10B H 0.5851 1.1074 0.8794 0.078 Uiso 1 1 calc R
H10C H 0.6336 1.1407 1.0088 0.078 Uiso 1 1 calc R
C11 C 0.4901(2) 0.8870(2) 0.8470(2) 0.0410(6) Uani 1 1 d .
O4 O 0.41609(16) 0.78371(16) 0.81232(18) 0.0503(5) Uani 1 1 d .
N3 N 0.59821(19) 0.92991(19) 0.8747(2) 0.0425(5) Uani 1 1 d .
H3B H 0.5953 0.9432 0.8215 0.051 Uiso 1 1 d R
C12 C 0.6482(2) 0.8655(2) 0.8723(3) 0.0436(7) Uani 1 1 d .
C13 C 0.5613(3) 0.7402(3) 0.7443(3) 0.0650(9) Uani 1 1 d .
H13A H 0.4846 0.6852 0.7252 0.097 Uiso 1 1 calc R
H13B H 0.6007 0.7045 0.7424 0.097 Uiso 1 1 calc R
H13C H 0.5428 0.7504 0.6829 0.097 Uiso 1 1 calc R
C14 C 0.6681(3) 0.8512(3) 0.9677(3) 0.0502(7) Uani 1 1 d .
H14A H 0.7238 0.9327 1.0492 0.075 Uiso 1 1 calc R
H14B H 0.7046 0.8125 0.9695 0.075 Uiso 1 1 calc R
H14C H 0.5887 0.7993 0.9460 0.075 Uiso 1 1 calc R
C15 C 0.7714(3) 0.9495(3) 0.9079(3) 0.0621(9) Uani 1 1 d .
H15A H 0.7585 0.9614 0.8481 0.093 Uiso 1 1 calc R
H15B H 0.8089 0.9118 0.9080 0.093 Uiso 1 1 calc R
H15C H 0.8262 1.0295 0.9904 0.093 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
O1 C1 N2 122.8(2)
O1 C1 C2 121.0(2)
N2 C1 C2 116.2(2)
C3 C2 C7 119.6(2)
C3 C2 C1 117.7(2)
C7 C2 C1 122.7(2)
C4 C3 C2 120.9(2)
C4 C3 H3 119.6
C2 C3 H3 119.6
C5 C4 C3 117.9(2)
C5 C4 H4 121.1
C3 C4 H4 121.1
C6 C5 C4 123.1(2)
C6 C5 N1 117.8(3)
C4 C5 N1 119.0(3)
O3 N1 O2 123.0(3)
O3 N1 C5 118.6(3)
O2 N1 C5 118.4(3)
C5 C6 C7 118.0(2)
C5 C6 H6 121.0
C7 C6 H6 121.0
C6 C7 C2 120.4(2)
C6 C7 H7 119.8
C2 C7 H7 119.8
C1 N2 C8 123.2(2)
C1 N2 H2A 105.9
C8 N2 H2A 106.0
C9 C8 N2 125.3(2)
C9 C8 H8 117.4
N2 C8 H8 117.4
C8 C9 C10 119.9(2)
C8 C9 C11 120.1(2)
C10 C9 C11 120.0(2)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O4 C11 N3 122.8(2)
O4 C11 C9 121.1(2)
N3 C11 C9 116.1(2)
C11 N3 C12 125.6(2)
C11 N3 H3B 105.2
C12 N3 H3B 105.4
N3 C12 C15 105.8(2)
N3 C12 C14 108.9(2)
C15 C12 C14 109.7(2)
N3 C12 C13 111.1(2)
C15 C12 C13 110.5(2)
C14 C12 C13 110.7(2)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.229(3)
C1 N2 1.358(3)
C1 C2 1.497(4)
C2 C3 1.385(3)
C2 C7 1.395(3)
C3 C4 1.380(4)
C3 H3 0.9500
C4 C5 1.379(4)
C4 H4 0.9500
C5 C6 1.377(4)
C5 N1 1.467(3)
N1 O3 1.219(3)
N1 O2 1.220(3)
C6 C7 1.382(4)
C6 H6 0.9500
C7 H7 0.9500
N2 C8 1.377(3)
N2 H2A 0.9200
C8 C9 1.334(3)
C8 H8 0.9500
C9 C10 1.497(3)
C9 C11 1.499(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 O4 1.251(3)
C11 N3 1.333(3)
N3 C12 1.492(3)
N3 H3B 0.9200
C12 C15 1.518(4)
C12 C14 1.520(3)
C12 C13 1.524(4)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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 20.1(3)
N2 C1 C2 C3 -160.9(2)
O1 C1 C2 C7 -158.4(2)
N2 C1 C2 C7 20.5(3)
C7 C2 C3 C4 1.6(4)
C1 C2 C3 C4 -177.0(2)
C2 C3 C4 C5 0.1(4)
C3 C4 C5 C6 -1.6(4)
C3 C4 C5 N1 177.9(2)
C6 C5 N1 O3 -10.5(4)
C4 C5 N1 O3 169.9(3)
C6 C5 N1 O2 169.8(2)
C4 C5 N1 O2 -9.8(4)
C4 C5 C6 C7 1.4(4)
N1 C5 C6 C7 -178.2(2)
C5 C6 C7 C2 0.4(4)
C3 C2 C7 C6 -1.8(4)
C1 C2 C7 C6 176.7(2)
O1 C1 N2 C8 -0.9(4)
C2 C1 N2 C8 -179.8(2)
C1 N2 C8 C9 -177.4(2)
N2 C8 C9 C10 -178.3(2)
N2 C8 C9 C11 -0.1(4)
C8 C9 C11 O4 -11.3(4)
C10 C9 C11 O4 166.9(2)
C8 C9 C11 N3 169.7(2)
C10 C9 C11 N3 -12.1(3)
O4 C11 N3 C12 -1.8(4)
C9 C11 N3 C12 177.2(2)
C11 N3 C12 C15 178.8(3)
C11 N3 C12 C14 -63.3(3)
C11 N3 C12 C13 58.8(3)
