#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/24/4102487.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_4102487
loop_
_publ_author_name
'Shunsuke Chiba'
'Line Zhang'
'Jian-Yuan Lee'
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_contact_author_email       shunsuke@ntu.edu.sg
_publ_contact_author_fax         '+65 6791 1961'
_publ_contact_author_phone       '+65 6513 8013'
_publ_section_title
;
 Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from
 α-Azido-N-arylamides under an Oxygen Atmosphere
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7266
_journal_page_last               7267
_journal_paper_doi               10.1021/ja1027327
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C19 H14 N2 O2'
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.445(8)
_cell_angle_beta                 73.634(7)
_cell_angle_gamma                76.889(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0717(9)
_cell_length_b                   10.4575(14)
_cell_length_c                   11.1343(15)
_cell_measurement_reflns_used    9445
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      34.36
_cell_measurement_theta_min      2.60
_cell_volume                     763.16(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      103(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34983
_diffrn_reflns_theta_full        34.64
_diffrn_reflns_theta_max         34.64
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         6466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0866P)²+0.0921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                5158
_reflns_number_total             6466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1027327_si_003.cif
_cod_data_source_block           4d_chiba20s
_cod_original_cell_volume        763.16(17)
_cod_database_code               4102487
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.33337(12) 0.88269(8) 1.03586(8) 0.01879(15) Uani 1 1 d .
H1 H 0.4637 0.9037 1.0035 0.023 Uiso 1 1 calc R
C2 C 0.19291(12) 0.95591(8) 1.12136(8) 0.01974(15) Uani 1 1 d .
H2 H 0.2263 1.0277 1.1474 0.024 Uiso 1 1 calc R
C3 C -0.00240(11) 0.92577(8) 1.17174(7) 0.01624(14) Uani 1 1 d .
C4 C -0.15225(13) 1.00013(8) 1.25976(8) 0.02039(15) Uani 1 1 d .
H4 H -0.1235 1.0737 1.2857 0.024 Uiso 1 1 calc R
C5 C -0.33850(13) 0.96698(9) 1.30792(8) 0.02203(16) Uani 1 1 d .
H5 H -0.4373 1.0175 1.3671 0.026 Uiso 1 1 calc R
C6 C -0.38432(12) 0.85840(9) 1.27018(9) 0.02292(17) Uani 1 1 d .
H6 H -0.5134 0.8359 1.3045 0.027 Uiso 1 1 calc R
C7 C -0.24362(12) 0.78510(9) 1.18432(8) 0.02061(16) Uani 1 1 d .
H7 H -0.2760 0.7124 1.1592 0.025 Uiso 1 1 calc R
C8 C -0.04963(11) 0.81716(8) 1.13268(7) 0.01562(14) Uani 1 1 d .
C9 C 0.09824(11) 0.74322(8) 1.04322(7) 0.01590(14) Uani 1 1 d .
H9 H 0.0677 0.6709 1.0163 0.019 Uiso 1 1 calc R
C10 C 0.28623(11) 0.77555(7) 0.99491(7) 0.01521(13) Uani 1 1 d .
C11 C 0.43945(11) 0.70438(8) 0.89944(7) 0.01515(13) Uani 1 1 d .
C12 C 0.44054(11) 0.56847(8) 0.87123(7) 0.01550(14) Uani 1 1 d .
C13 C 0.66788(13) 0.42979(9) 0.71044(9) 0.02267(17) Uani 1 1 d .
H13A H 0.6014 0.3586 0.7628 0.034 Uiso 1 1 calc R
H13B H 0.8136 0.4014 0.6957 0.034 Uiso 1 1 calc R
H13C H 0.6315 0.4502 0.6295 0.034 Uiso 1 1 calc R
C14 C 0.71418(11) 0.65542(8) 0.74395(7) 0.01642(14) Uani 1 1 d .
C15 C 0.91368(12) 0.61057(8) 0.77684(8) 0.01936(15) Uani 1 1 d .
H15 H 0.9180 0.5612 0.8569 0.023 Uiso 1 1 calc R
C16 C 1.08410(12) 0.63768(10) 0.69762(8) 0.02316(17) Uani 1 1 d .
H16 H 1.2060 0.6067 0.7227 0.028 Uiso 1 1 calc R
C17 C 1.08861(13) 0.71397(9) 0.57277(8) 0.02244(17) Uani 1 1 d .
C18 C 0.90101(13) 0.74515(9) 0.53143(8) 0.02257(16) Uani 1 1 d .
H18 H 0.9024 0.7855 0.4476 0.027 Uiso 1 1 calc R
C19 C 0.72931(12) 0.71797(9) 0.60923(8) 0.02014(15) Uani 1 1 d .
H19 H 0.6120 0.7388 0.5785 0.024 Uiso 1 1 calc R
N1 N 0.59186(10) 0.75303(7) 0.82833(7) 0.01736(13) Uani 1 1 d .
N2 N 0.60468(10) 0.54670(7) 0.77453(7) 0.01746(13) Uani 1 1 d .
O1 O 0.32207(9) 0.49334(6) 0.92214(6) 0.01946(13) Uani 1 1 d .
O2 O 1.24284(11) 0.74958(9) 0.50634(7) 0.03370(18) Uani 1 1 d .
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 C10 120.58(7)
C2 C1 H1 119.7
C10 C1 H1 119.7
C1 C2 C3 120.72(7)
C1 C2 H2 119.6
C3 C2 H2 119.6
C4 C3 C2 122.27(7)
C4 C3 C8 118.74(7)
C2 C3 C8 118.99(7)
C5 C4 C3 120.70(8)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 120.48(8)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 120.36(8)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C8 120.43(8)
C6 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C7 121.50(7)
C9 C8 C3 119.23(7)
C7 C8 C3 119.27(7)
C10 C9 C8 120.53(7)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C1 119.94(7)
C9 C10 C11 121.88(7)
C1 C10 C11 118.17(7)
N1 C11 C10 122.68(7)
N1 C11 C12 112.10(7)
C10 C11 C12 125.22(7)
O1 C12 N2 126.93(7)
O1 C12 C11 129.32(7)
N2 C12 C11 103.75(6)
N2 C13 H13A 109.5
N2 C13 H13B 109.5
H13A C13 H13B 109.5
N2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N2 C14 N1 104.80(6)
N2 C14 C19 111.09(7)
N1 C14 C19 108.72(6)
N2 C14 C15 110.44(7)
N1 C14 C15 107.42(6)
C19 C14 C15 113.88(6)
C16 C15 C14 122.37(8)
C16 C15 H15 118.8
C14 C15 H15 118.8
C15 C16 C17 121.81(8)
C15 C16 H16 119.1
C17 C16 H16 119.1
O2 C17 C16 120.89(9)
O2 C17 C18 121.98(9)
C16 C17 C18 117.13(7)
C19 C18 C17 121.42(8)
C19 C18 H18 119.3
C17 C18 H18 119.3
C18 C19 C14 122.54(8)
C18 C19 H19 118.7
C14 C19 H19 118.7
C11 N1 C14 108.07(6)
C12 N2 C13 125.03(7)
C12 N2 C14 111.17(6)
C13 N2 C14 123.79(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3669(11)
C1 C10 1.4200(11)
C1 H1 0.9500
C2 C3 1.4205(11)
C2 H2 0.9500
C3 C4 1.4170(11)
C3 C8 1.4233(11)
C4 C5 1.3724(12)
C4 H4 0.9500
C5 C6 1.4105(13)
C5 H5 0.9500
C6 C7 1.3703(12)
C6 H6 0.9500
C7 C8 1.4208(11)
C7 H7 0.9500
C8 C9 1.4183(11)
C9 C10 1.3802(10)
C9 H9 0.9500
C10 C11 1.4604(11)
C11 N1 1.2913(10)
C11 C12 1.5087(11)
C12 O1 1.2282(9)
C12 N2 1.3506(10)
C13 N2 1.4476(11)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 N2 1.4550(10)
C14 N1 1.4716(10)
C14 C19 1.5070(12)
C14 C15 1.5075(11)
C15 C16 1.3323(12)
C15 H15 0.9500
C16 C17 1.4663(13)
C16 H16 0.9500
C17 O2 1.2264(10)
C17 C18 1.4734(13)
C18 C19 1.3338(11)
C18 H18 0.9500
C19 H19 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660110
