#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:52:41 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178795 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/49/4104996.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_4104996
loop_
_publ_author_name
'Yi-Feng Wang'
'Shunsuke Chiba'
_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
;
 Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis
 of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12570
_journal_page_last               12572
_journal_paper_doi               10.1021/ja905110c
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C15 H19 N O'
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 124.361(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.9491(8)
_cell_length_b                   11.4791(4)
_cell_length_c                   12.8044(5)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.36
_cell_volume                     2541.84(18)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19880
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0470
_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)+(0.0512P)²+0.6891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                2496
_reflns_number_total             3896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905110c_si_006.cif
_cod_data_source_block           chiba-6ha
_cod_original_cell_volume        2541.84(16)
_cod_database_code               4104996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.41159(8) 0.54234(12) 0.30936(13) 0.0559(4) Uani 1 1 d .
H1A H 0.4581 0.5586 0.3126 0.067 Uiso 1 1 calc R
H1B H 0.4168 0.5795 0.3818 0.067 Uiso 1 1 calc R
C2 C 0.40387(8) 0.41138(12) 0.31735(13) 0.0575(4) Uani 1 1 d .
H2A H 0.3638 0.3959 0.3315 0.069 Uiso 1 1 calc R
H2B H 0.4521 0.3807 0.3890 0.069 Uiso 1 1 calc R
C3 C 0.38386(7) 0.34895(11) 0.19711(12) 0.0478(3) Uani 1 1 d .
H3A H 0.3713 0.2683 0.2005 0.057 Uiso 1 1 calc R
H3B H 0.4286 0.3497 0.1928 0.057 Uiso 1 1 calc R
C4 C 0.31566(6) 0.40604(9) 0.07821(11) 0.0348(3) Uani 1 1 d .
C5 C 0.33180(7) 0.53375(10) 0.07362(12) 0.0414(3) Uani 1 1 d .
H5A H 0.2891 0.5686 -0.0037 0.050 Uiso 1 1 calc R
H5B H 0.3784 0.5424 0.0752 0.050 Uiso 1 1 calc R
C6 C 0.34187(7) 0.59388(10) 0.18793(12) 0.0419(3) Uani 1 1 d .
H6 H 0.3518 0.6768 0.1846 0.050 Uiso 1 1 calc R
C7 C 0.26680(7) 0.58251(9) 0.18117(11) 0.0376(3) Uani 1 1 d .
H7 H 0.2803 0.5875 0.2678 0.045 Uiso 1 1 calc R
C8 C 0.21091(8) 0.68262(11) 0.10572(15) 0.0577(4) Uani 1 1 d .
H8A H 0.1986 0.6825 0.0213 0.087 Uiso 1 1 calc R
H8B H 0.2347 0.7554 0.1460 0.087 Uiso 1 1 calc R
H8C H 0.1644 0.6727 0.1027 0.087 Uiso 1 1 calc R
C9 C 0.22654(6) 0.46626(9) 0.12686(10) 0.0322(2) Uani 1 1 d .
C10 C 0.15717(6) 0.44089(9) 0.12836(11) 0.0363(3) Uani 1 1 d .
C11 C 0.09704(7) 0.37418(11) 0.03285(13) 0.0449(3) Uani 1 1 d .
H11 H 0.0994 0.3476 -0.0335 0.054 Uiso 1 1 calc R
C12 C 0.03381(8) 0.34698(12) 0.03564(16) 0.0571(4) Uani 1 1 d .
H12 H -0.0064 0.3032 -0.0295 0.068 Uiso 1 1 calc R
C13 C 0.02988(8) 0.38414(13) 0.13410(16) 0.0606(4) Uani 1 1 d .
H13 H -0.0122 0.3640 0.1368 0.073 Uiso 1 1 calc R
C14 C 0.08859(9) 0.45128(13) 0.22831(15) 0.0583(4) Uani 1 1 d .
H14 H 0.0860 0.4770 0.2947 0.070 Uiso 1 1 calc R
C15 C 0.15127(7) 0.48088(12) 0.22527(12) 0.0456(3) Uani 1 1 d .
H15 H 0.1900 0.5280 0.2885 0.055 Uiso 1 1 calc R
N1 N 0.24664(5) 0.38847(8) 0.07908(8) 0.0327(2) Uani 1 1 d .
O1 O 0.30223(5) 0.35369(7) -0.03254(8) 0.0451(2) Uani 1 1 d .
H1 H 0.2911 0.2849 -0.0346 0.068 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 111.96(10)
C1 C2 C3 112.03(12)
C2 C3 C4 111.95(10)
O1 C4 N1 108.07(9)
O1 C4 C5 107.16(9)
N1 C4 C5 112.12(9)
O1 C4 C3 111.21(10)
N1 C4 C3 107.76(9)
C5 C4 C3 110.52(10)
C4 C5 C6 108.35(10)
C5 C6 C1 109.69(11)
C5 C6 C7 109.07(10)
C1 C6 C7 112.69(11)
C9 C7 C6 112.80(9)
C9 C7 C8 109.91(10)
C6 C7 C8 111.51(10)
N1 C9 C10 117.07(10)
N1 C9 C7 125.67(10)
C10 C9 C7 117.25(9)
C11 C10 C15 118.28(11)
C11 C10 C9 120.12(11)
C15 C10 C9 121.59(11)
C12 C11 C10 120.55(13)
C13 C12 C11 120.51(13)
C14 C13 C12 119.43(13)
C13 C14 C15 120.58(14)
C14 C15 C10 120.61(13)
C9 N1 C4 119.96(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.522(2)
C1 C6 1.5288(18)
C2 C3 1.527(2)
C3 C4 1.5275(16)
C4 O1 1.4145(14)
C4 N1 1.4662(14)
C4 C5 1.5130(16)
C5 C6 1.5216(17)
C6 C7 1.5311(16)
C7 C9 1.5211(15)
C7 C8 1.5323(17)
C9 N1 1.2806(14)
C9 C10 1.4928(15)
C10 C11 1.3891(17)
C10 C15 1.3925(17)
C11 C12 1.3810(18)
C12 C13 1.377(2)
C13 C14 1.374(2)
C14 C15 1.3780(18)
