#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152690.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_7152690
loop_
_publ_author_name
'Hodges, Alastair J.'
'Adams, Joseph P.'
'Bond, Andrew D.'
'Holmes, Andrew B.'
'Press, Neil J.'
'Roughley, Stephen D.'
'Ryan, John H.'
'Saubern, Simon'
'Smith, Catherine J.'
'Turnbull, Michael D.'
'Newton, Annabella F.'
_publ_section_title
;
 Intramolecular nitrone dipolar cycloadditions: control of
 regioselectivity and synthesis of naturally-occurring spirocyclic
 alkaloids.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8963
_journal_page_last               8974
_journal_paper_doi               10.1039/c2ob26333e
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.279(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4675(15)
_cell_length_b                   11.662(2)
_cell_length_c                   8.6820(16)
_cell_measurement_reflns_used    5022
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      3.4
_cell_volume                     834.4(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '0.15 deg step phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'synchrotron gapped beam'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6885
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7499
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_correction_T_min  0.9968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
In the absence of significant anomalous scattering effects, the absolute
structure is not determined. Friedel pairs have *not* been merged.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0643
_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)+(0.1018P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                3224
_reflns_number_total             3867
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ob26333e.txt
_cod_data_source_block           cam49
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7152690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
N1 N 0.09780(19) -0.02584(17) 0.7385(2) 0.0208(4) Uani 1 1 d .
C1 C -0.0230(2) -0.1202(2) 0.6985(3) 0.0213(4) Uani 1 1 d .
C2 C 0.0113(3) -0.2188(2) 0.8187(3) 0.0299(5) Uani 1 1 d .
H2A H -0.0875 -0.2667 0.8045 0.036 Uiso 1 1 calc R
H2B H 0.0982 -0.2674 0.7940 0.036 Uiso 1 1 calc R
C3 C 0.0617(3) -0.1835(3) 0.9908(3) 0.0349(6) Uani 1 1 d .
H3A H -0.0321 -0.1499 1.0250 0.042 Uiso 1 1 calc R
H3B H 0.0994 -0.2514 1.0576 0.042 Uiso 1 1 calc R
C4 C 0.1971(3) -0.0962(2) 1.0100(3) 0.0312(5) Uani 1 1 d .
H4A H 0.2923 -0.1314 0.9805 0.037 Uiso 1 1 calc R
H4B H 0.2300 -0.0722 1.1222 0.037 Uiso 1 1 calc R
C5 C 0.1431(2) 0.0081(2) 0.9068(3) 0.0227(4) Uani 1 1 d .
H5A H 0.0469 0.0434 0.9371 0.027 Uiso 1 1 calc R
C6 C -0.0182(3) -0.1673(2) 0.5340(3) 0.0273(5) Uani 1 1 d .
H6A H 0.0851 -0.2091 0.5422 0.033 Uiso 1 1 calc R
H6B H -0.1077 -0.2231 0.5012 0.033 Uiso 1 1 calc R
C7 C -0.0332(3) -0.0758(3) 0.4062(3) 0.0351(6) Uani 1 1 d .
H7A H 0.0718 -0.0353 0.4194 0.042 Uiso 1 1 calc R
H7B H -0.0573 -0.1132 0.3011 0.042 Uiso 1 1 calc R
C8 C -0.1652(3) 0.0109(3) 0.4119(3) 0.0345(6) Uani 1 1 d .
H8A H -0.1523 0.0792 0.3481 0.041 Uiso 1 1 calc R
H8B H -0.2731 -0.0231 0.3673 0.041 Uiso 1 1 calc R
C9 C -0.1527(2) 0.0457(2) 0.5826(3) 0.0279(5) Uani 1 1 d .
H9A H -0.2280 0.1105 0.5895 0.034 Uiso 1 1 calc R
C10 C -0.1885(2) -0.0576(2) 0.6762(3) 0.0256(5) Uani 1 1 d .
H10A H -0.2749 -0.1052 0.6074 0.031 Uiso 1 1 calc R
O1 O 0.01375(18) 0.07589(15) 0.65616(19) 0.0267(4) Uani 1 1 d .
C11 C -0.2410(3) -0.0254(2) 0.8202(3) 0.0325(5) Uani 1 1 d .
N2 N -0.2899(3) 0.0022(3) 0.9270(3) 0.0475(7) Uani 1 1 d .
C12 C 0.2785(3) 0.0968(2) 0.9264(3) 0.0275(5) Uani 1 1 d .
H12A H 0.3773 0.0625 0.9030 0.033 Uiso 1 1 calc R
H12B H 0.2443 0.1625 0.8542 0.033 Uiso 1 1 calc R
C13 C 0.4519(3) 0.1969(2) 1.1385(3) 0.0263(5) Uani 1 1 d .
H13A H 0.4425 0.2716 1.0829 0.032 Uiso 1 1 calc R
H13B H 0.5454 0.1549 1.1156 0.032 Uiso 1 1 calc R
C14 C 0.4763(2) 0.2155(2) 1.3137(3) 0.0222(4) Uani 1 1 d .
C15 C 0.3998(3) 0.1450(2) 1.4040(3) 0.0275(5) Uani 1 1 d .
H15A H 0.3316 0.0847 1.3539 0.033 Uiso 1 1 calc R
C16 C 0.4214(3) 0.1614(2) 1.5642(3) 0.0334(6) Uani 1 1 d .
H16A H 0.3688 0.1120 1.6238 0.040 Uiso 1 1 calc R
C17 C 0.5192(3) 0.2492(2) 1.6393(3) 0.0316(6) Uani 1 1 d .
H17A H 0.5334 0.2609 1.7500 0.038 Uiso 1 1 calc R
C18 C 0.5968(3) 0.3204(2) 1.5505(3) 0.0312(5) Uani 1 1 d .
H18A H 0.6646 0.3808 1.6011 0.037 Uiso 1 1 calc R
C19 C 0.5756(2) 0.3036(2) 1.3894(3) 0.0261(5) Uani 1 1 d .
H19A H 0.6290 0.3524 1.3299 0.031 Uiso 1 1 calc R
O2 O 0.30856(19) 0.13295(19) 1.0867(2) 0.0359(5) 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
C5 N1 O1 104.47(16)
C5 N1 C1 115.96(17)
O1 N1 C1 104.56(14)
N1 C1 C2 112.49(17)
N1 C1 C6 108.52(17)
C2 C1 C6 108.8(2)
N1 C1 C10 103.51(17)
C2 C1 C10 117.49(19)
C6 C1 C10 105.52(18)
C3 C2 C1 115.7(2)
C4 C3 C2 109.0(2)
C3 C4 C5 110.90(19)
N1 C5 C4 110.09(19)
N1 C5 C12 108.06(17)
C4 C5 C12 111.18(18)
C7 C6 C1 114.2(2)
C8 C7 C6 112.4(2)
C9 C8 C7 108.9(2)
O1 C9 C8 109.75(19)
O1 C9 C10 104.46(17)
C8 C9 C10 109.5(2)
C11 C10 C9 112.9(2)
C11 C10 C1 117.1(2)
C9 C10 C1 98.84(17)
C9 O1 N1 109.19(16)
N2 C11 C10 176.0(3)
O2 C12 C5 105.75(17)
O2 C13 C14 107.91(18)
C19 C14 C15 118.5(2)
C19 C14 C13 120.7(2)
C15 C14 C13 120.7(2)
C16 C15 C14 121.1(2)
C15 C16 C17 120.4(2)
C16 C17 C18 119.2(2)
C19 C18 C17 120.4(2)
C18 C19 C14 120.4(2)
C13 O2 C12 114.68(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.477(3)
N1 O1 1.480(2)
N1 C1 1.488(3)
C1 C2 1.535(3)
C1 C6 1.539(3)
C1 C10 1.553(3)
C2 C3 1.514(4)
C3 C4 1.514(4)
C4 C5 1.517(3)
C5 C12 1.524(3)
C6 C7 1.524(4)
C7 C8 1.517(4)
C8 C9 1.516(4)
C9 O1 1.451(3)
C9 C10 1.522(4)
C10 C11 1.468(3)
C11 N2 1.145(3)
C12 O2 1.420(3)
C13 O2 1.407(3)
C13 C14 1.503(3)
C14 C19 1.393(3)
C14 C15 1.393(3)
C15 C16 1.374(3)
C16 C17 1.383(4)
C17 C18 1.396(4)
C18 C19 1.383(3)
