#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/67/1506722.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_1506722
loop_
_publ_author_name
'Blakemore, Paul R.'
'Kilner, Colin'
'Norcross, Neil R.'
'Astles, Peter C.'
_publ_section_title
;
 A practical synthesis of (+/-)-alpha-isosparteine from a
 tetraoxobispidine core.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4721
_journal_page_last               4724
_journal_paper_doi               10.1021/ol0519184
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C15 H18 N2 O4'
_chemical_formula_sum            'C15 H18 N2 O4'
_chemical_formula_weight         290.31
_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                   8.5596(8)
_cell_length_b                   11.4819(12)
_cell_length_c                   26.250(3)
_cell_measurement_reflns_used    5282
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      1.00
_cell_volume                     2579.9(5)
_computing_cell_refinement
;
APEX 2 software, Bruker Nonius 2004 
;
_computing_data_collection
;
APEX 2 software, Bruker Nonius 2004 
;
_computing_data_reduction
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004 
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean
;
120 microns
;
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_detector       'Apex camera'
_diffrn_radiation_monochromator
;
graphite model mounted in "parallel" mode
;
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            29091
_diffrn_reflns_theta_full        25.43
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0336
_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)+(0.0451P)²+0.7888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                1870
_reflns_number_total             2370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0519184si20050809_053137.cif
_cod_data_source_block           cmpd9
_cod_database_code               1506722
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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
O9' O 0.16877(12) 0.97318(9) 0.46831(4) 0.0197(3) Uani 1 1 d .
H9' H 0.1618 1.0081 0.4963 0.030 Uiso 1 1 calc R
O9 O -0.11317(12) 0.95766(9) 0.28198(4) 0.0210(3) Uani 1 1 d .
H9 H -0.0997 0.9413 0.2511 0.032 Uiso 1 1 calc R
O3' O 0.38968(12) 0.92828(9) 0.32088(4) 0.0220(3) Uani 1 1 d .
O3 O -0.16040(12) 0.93562(10) 0.43531(4) 0.0241(3) Uani 1 1 d .
N4 N -0.05333(14) 0.88145(10) 0.36049(4) 0.0166(3) Uani 1 1 d .
N4' N 0.30334(14) 1.00763(11) 0.39431(4) 0.0172(3) Uani 1 1 d .
C3' C 0.28470(17) 0.97897(13) 0.34492(5) 0.0165(3) Uani 1 1 d .
C9 C 0.01525(17) 0.91505(13) 0.31102(5) 0.0171(3) Uani 1 1 d .
C2' C 0.13365(17) 1.01513(13) 0.31847(5) 0.0169(3) Uani 1 1 d .
H2' H 0.1624 1.0445 0.2838 0.020 Uiso 1 1 calc R
C3 C -0.06953(17) 0.95689(13) 0.39994(5) 0.0176(3) Uani 1 1 d .
C7' C 0.40541(18) 1.17374(14) 0.46343(6) 0.0239(4) Uani 1 1 d .
H7' H 0.4444 1.2373 0.4828 0.029 Uiso 1 1 calc R
C2 C 0.02546(17) 1.06911(13) 0.40014(6) 0.0176(3) Uani 1 1 d .
H2 H -0.0371 1.1293 0.4186 0.021 Uiso 1 1 calc R
C9' C 0.18244(17) 1.05558(13) 0.42859(5) 0.0172(3) Uani 1 1 d .
C6' C 0.50225(19) 1.08934(14) 0.45097(6) 0.0231(4) Uani 1 1 d .
H6' H 0.6065 1.0930 0.4633 0.028 Uiso 1 1 calc R
C7 C -0.00688(19) 0.70234(14) 0.28931(6) 0.0243(4) Uani 1 1 d .
H7 H 0.0158 0.6387 0.2674 0.029 Uiso 1 1 calc R
C8' C 0.23699(18) 1.17416(13) 0.44844(6) 0.0209(4) Uani 1 1 d .
H8'A H 0.2204 1.2336 0.4217 0.025 Uiso 1 1 calc R
H8'B H 0.1728 1.1962 0.4783 0.025 Uiso 1 1 calc R
C6 C -0.12226(19) 0.69183(14) 0.32225(6) 0.0249(4) Uani 1 1 d .
H6 H -0.1792 0.6208 0.3228 0.030 Uiso 1 1 calc R
C8 C 0.08939(18) 0.80986(13) 0.28499(6) 0.0216(4) Uani 1 1 d .
H8A H 0.1055 0.8280 0.2485 0.026 Uiso 1 1 calc R
H8B H 0.1932 0.7952 0.3004 0.026 Uiso 1 1 calc R
C5 C -0.16839(18) 0.78560(14) 0.35879(6) 0.0227(4) Uani 1 1 d .
H5A H -0.2714 0.8173 0.3487 0.027 Uiso 1 1 calc R
H5B H -0.1792 0.7517 0.3933 0.027 Uiso 1 1 calc R
C5' C 0.45676(17) 0.98787(14) 0.41835(6) 0.0210(4) Uani 1 1 d .
H5'A H 0.5367 0.9760 0.3916 0.025 Uiso 1 1 calc R
H5'B H 0.4524 0.9165 0.4395 0.025 Uiso 1 1 calc R
C1 C 0.05448(18) 1.11428(13) 0.34643(5) 0.0192(3) Uani 1 1 d .
H1A H -0.0453 1.1352 0.3297 0.023 Uiso 1 1 calc R
H1B H 0.1227 1.1839 0.3472 0.023 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
C9' O9' H9' 109.5
C9 O9 H9 109.5
C3 N4 C9 123.02(12)
C3 N4 C5 115.49(12)
C9 N4 C5 115.66(11)
C3' N4' C5' 118.68(12)
C3' N4' C9' 126.45(12)
C5' N4' C9' 114.86(11)
O3' C3' N4' 121.16(13)
O3' C3' C2' 120.62(12)
N4' C3' C2' 118.17(12)
O9 C9 N4 104.69(11)
O9 C9 C8 110.69(12)
N4 C9 C8 110.63(12)
O9 C9 C2' 108.58(11)
N4 C9 C2' 110.11(11)
C8 C9 C2' 111.88(12)
C1 C2' C3' 111.31(12)
C1 C2' C9 109.08(12)
C3' C2' C9 114.29(12)
C1 C2' H2' 107.3
C3' C2' H2' 107.3
C9 C2' H2' 107.3
O3 C3 N4 120.76(14)
O3 C3 C2 120.04(13)
N4 C3 C2 119.19(13)
C6' C7' C8' 122.98(14)
C6' C7' H7' 118.5
C8' C7' H7' 118.5
C1 C2 C3 111.84(12)
C1 C2 C9' 109.88(12)
C3 C2 C9' 112.38(12)
C1 C2 H2 107.5
C3 C2 H2 107.5
C9' C2 H2 107.5
O9' C9' N4' 104.95(11)
O9' C9' C8' 111.70(12)
N4' C9' C8' 108.97(12)
O9' C9' C2 110.61(12)
N4' C9' C2 110.61(11)
C8' C9' C2 109.90(12)
C7' C6' C5' 123.44(14)
C7' C6' H6' 118.3
C5' C6' H6' 118.3
C6 C7 C8 122.72(14)
C6 C7 H7 118.6
C8 C7 H7 118.6
C7' C8' C9' 112.40(13)
C7' C8' H8'A 109.1
C9' C8' H8'A 109.1
C7' C8' H8'B 109.1
C9' C8' H8'B 109.1
H8'A C8' H8'B 107.9
C7 C6 C5 123.56(15)
C7 C6 H6 118.2
C5 C6 H6 118.2
C7 C8 C9 113.09(13)
C7 C8 H8A 109.0
C9 C8 H8A 109.0
C7 C8 H8B 109.0
C9 C8 H8B 109.0
H8A C8 H8B 107.8
N4 C5 C6 112.32(13)
N4 C5 H5A 109.1
C6 C5 H5A 109.1
N4 C5 H5B 109.1
C6 C5 H5B 109.1
H5A C5 H5B 107.9
N4' C5' C6' 110.89(12)
N4' C5' H5'A 109.5
C6' C5' H5'A 109.5
N4' C5' H5'B 109.5
C6' C5' H5'B 109.5
H5'A C5' H5'B 108.0
C2' C1 C2 105.40(12)
C2' C1 H1A 110.7
C2 C1 H1A 110.7
C2' C1 H1B 110.7
C2 C1 H1B 110.7
H1A C1 H1B 108.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O9' C9' 1.4127(18)
O9' H9' 0.8400
O9 C9 1.4244(17)
O9 H9 0.8400
O3' C3' 1.2428(17)
O3 C3 1.2355(18)
N4 C3 1.3573(19)
N4 C9 1.4764(18)
N4 C5 1.4775(19)
N4' C3' 1.3472(18)
N4' C5' 1.4746(18)
N4' C9' 1.4778(18)
C3' C2' 1.525(2)
C9 C8 1.526(2)
C9 C2' 1.545(2)
C2' C1 1.515(2)
C2' H2' 1.0000
C3 C2 1.524(2)
C7' C6' 1.317(2)
C7' C8' 1.494(2)
C7' H7' 0.9500
C2 C1 1.523(2)
C2 C9' 1.545(2)
C2 H2 1.0000
C9' C8' 1.531(2)
C6' C5' 1.497(2)
C6' H6' 0.9500
C7 C6 1.318(2)
C7 C8 1.489(2)
C7 H7 0.9500
C8' H8'A 0.9900
C8' H8'B 0.9900
C6 C5 1.495(2)
C6 H6 0.9500
C8 H8A 0.9900
C8 H8B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C5' H5'A 0.9900
C5' H5'B 0.9900
C1 H1A 0.9900
C1 H1B 0.9900
