#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:19:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178465 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/86/4028695.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_4028695
loop_
_publ_author_name
'Kiran Indukuri'
'R. Unnava'
'Manash J. Deka'
'Anil K. Saikia'
_publ_section_title
;
 Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via
 a Tandem Aza Prins-Ritter/Friedel-Crafts Type Reaction of Endocyclic
 N-Acyliminium Ions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10629
_journal_page_last               10641
_journal_paper_doi               10.1021/jo401450j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C17 H22 N2 O2'
_chemical_formula_weight         286.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0817(14)
_cell_length_b                   9.5974(10)
_cell_length_c                   23.030(2)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.63
_cell_measurement_theta_min      2.01
_cell_volume                     3112.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34737
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colour-less
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0430
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                2274
_reflns_number_total             2869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401450j_si_003.cif
_cod_data_source_block           kir1
_cod_database_code               4028695
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C10 C 0.64352(10) -0.02659(15) 0.40456(6) 0.0482(4) Uani 1 1 d .
H10 H 0.6680 -0.0157 0.3650 0.058 Uiso 1 1 calc R
C8 C 0.50975(9) 0.14883(15) 0.38672(6) 0.0457(4) Uani 1 1 d .
H8 H 0.4750 0.2211 0.4080 0.055 Uiso 1 1 calc R
C6 C 0.44799(10) 0.26468(14) 0.29627(5) 0.0461(4) Uani 1 1 d .
C11 C 0.57108(11) -0.14406(15) 0.40459(6) 0.0531(4) Uani 1 1 d .
H11A H 0.5481 -0.1593 0.4438 0.064 Uiso 1 1 calc R
H11B H 0.6008 -0.2294 0.3912 0.064 Uiso 1 1 calc R
C3 C 0.28364(11) 0.36986(17) 0.24532(7) 0.0591(4) Uani 1 1 d .
H3 H 0.2281 0.4043 0.2288 0.071 Uiso 1 1 calc R
C1 C 0.39826(10) 0.18847(16) 0.25520(6) 0.0533(4) Uani 1 1 d .
H1 H 0.4199 0.1005 0.2446 0.064 Uiso 1 1 calc R
C9 C 0.59733(10) 0.10996(16) 0.42277(6) 0.0520(4) Uani 1 1 d .
H9A H 0.6438 0.1841 0.4195 0.062 Uiso 1 1 calc R
H9B H 0.5789 0.1033 0.4633 0.062 Uiso 1 1 calc R
C15 C 0.36462(11) 0.01708(18) 0.41040(6) 0.0532(4) Uani 1 1 d .
C12 C 0.48811(10) -0.10737(15) 0.36498(6) 0.0513(4) Uani 1 1 d .
H12 H 0.5100 -0.1019 0.3247 0.062 Uiso 1 1 calc R
C7 C 0.53420(10) 0.20749(16) 0.32655(6) 0.0540(4) Uani 1 1 d .
H7A H 0.5810 0.2809 0.3307 0.065 Uiso 1 1 calc R
H7B H 0.5619 0.1343 0.3030 0.065 Uiso 1 1 calc R
C5 C 0.41417(11) 0.39566(15) 0.31036(6) 0.0560(4) Uani 1 1 d .
H5 H 0.4472 0.4495 0.3372 0.067 Uiso 1 1 calc R
C2 C 0.31690(11) 0.24135(18) 0.22981(6) 0.0586(4) Uani 1 1 d .
H2 H 0.2847 0.1892 0.2021 0.070 Uiso 1 1 calc R
C4 C 0.33258(12) 0.44820(17) 0.28548(7) 0.0622(5) Uani 1 1 d .
H4 H 0.3107 0.5362 0.2958 0.075 Uiso 1 1 calc R
C14 C 0.33108(12) -0.1301(2) 0.40669(8) 0.0721(5) Uani 1 1 d .
H14A H 0.2681 -0.1343 0.3897 0.086 Uiso 1 1 calc R
H14B H 0.3289 -0.1721 0.4450 0.086 Uiso 1 1 calc R
C13 C 0.40173(14) -0.2041(2) 0.36890(8) 0.0767(5) Uani 1 1 d .
H13A H 0.3753 -0.2209 0.3306 0.092 Uiso 1 1 calc R
H13B H 0.4195 -0.2928 0.3859 0.092 Uiso 1 1 calc R
C16 C 0.81257(11) -0.02285(16) 0.42945(7) 0.0540(4) Uani 1 1 d .
C17 C 0.88157(13) -0.0303(2) 0.47900(8) 0.0760(5) Uani 1 1 d .
H17A H 0.9389 -0.0750 0.4663 0.114 Uiso 1 1 calc R
H17B H 0.8541 -0.0829 0.5102 0.114 Uiso 1 1 calc R
H17C H 0.8959 0.0622 0.4922 0.114 Uiso 1 1 calc R
N1 N 0.44858(8) 0.02730(11) 0.38287(4) 0.0437(3) Uani 1 1 d .
N2 N 0.72297(8) -0.05665(14) 0.44293(6) 0.0556(4) Uani 1 1 d .
O2 O 0.83750(9) 0.01163(14) 0.38055(5) 0.0756(4) Uani 1 1 d .
O1 O 0.32507(7) 0.11379(13) 0.43603(5) 0.0728(4) Uani 1 1 d .
H1A H 0.7076(11) -0.0770(17) 0.4795(8) 0.066(5) Uiso 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
N2 C10 C11 111.64(11)
N2 C10 C9 109.40(11)
C11 C10 C9 110.58(12)
N1 C8 C9 108.35(11)
N1 C8 C7 111.87(11)
C9 C8 C7 113.44(11)
C5 C6 C1 117.78(13)
C5 C6 C7 120.06(13)
C1 C6 C7 122.13(13)
C10 C11 C12 110.05(11)
C2 C3 C4 119.79(15)
C2 C1 C6 120.90(14)
C10 C9 C8 113.84(11)
O1 C15 N1 124.59(15)
O1 C15 C14 126.68(14)
N1 C15 C14 108.68(14)
N1 C12 C11 109.06(11)
N1 C12 C13 102.48(13)
C11 C12 C13 115.67(13)
C6 C7 C8 111.81(11)
C4 C5 C6 121.45(14)
C3 C2 C1 120.30(15)
C3 C4 C5 119.76(15)
C15 C14 C13 105.75(13)
C14 C13 C12 105.88(14)
O2 C16 N2 123.26(14)
O2 C16 C17 121.76(15)
N2 C16 C17 114.98(15)
C15 N1 C8 123.43(12)
C15 N1 C12 113.69(12)
C8 N1 C12 119.98(11)
C16 N2 C10 122.40(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C10 N2 1.4546(17)
C10 C11 1.520(2)
C10 C9 1.522(2)
C8 N1 1.4527(17)
C8 C9 1.5327(18)
C8 C7 1.5348(19)
C6 C5 1.383(2)
C6 C1 1.386(2)
C6 C7 1.5038(19)
C11 C12 1.5235(19)
C3 C2 1.367(2)
C3 C4 1.377(2)
C1 C2 1.383(2)
C15 O1 1.2328(18)
C15 N1 1.3452(19)
C15 C14 1.492(2)
C12 N1 1.4664(18)
C12 C13 1.533(2)
C5 C4 1.379(2)
C14 C13 1.500(3)
C16 O2 1.2251(19)
C16 N2 1.339(2)
C16 C17 1.501(2)
