#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:21:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180258 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/44/7114457.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_7114457
loop_
_publ_author_name
'Edwards, Andrew S.'
'Wybrow, Robert A. J.'
'Johnstone, Craig'
'Adams, Harry'
'Harrity, Joseph P. A.'
_publ_section_title
;
 A new approach to functionalised spiropiperidines through tandem RCM and
 nitrogen-directed reactionsElectronic supplementary information
 available: experimental procedures and data for all new compounds. See
 http://www.rsc.org/suppdata/cc/b2/b203851j/
;
_journal_issue                   14
_journal_name_full               'Chemical Communications'
_journal_page_first              1542
_journal_paper_doi               10.1039/b203851j
_journal_year                    2002
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.160(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.882(3)
_cell_length_b                   9.5188(19)
_cell_length_c                   13.700(3)
_cell_measurement_reflns_used    2011
_cell_measurement_temperature    150(2)
_cell_volume                     1537.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6647
_diffrn_reflns_theta_full        23.33
_diffrn_reflns_theta_max         23.33
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.264
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0737
_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)+(0.1311P)²+1.4352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2047
_refine_ls_wR_factor_ref         0.2270
_reflns_number_gt                1562
_reflns_number_total             2224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b203851j.txt
_cod_data_source_block           ohj46m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7114457
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.3810(2) 0.0734(3) 0.5424(2) 0.0377(8) Uani 1 1 d .
O2 O 0.8692(3) 0.2291(4) 0.8486(3) 0.0586(10) Uani 1 1 d .
O3 O 0.7592(3) 0.2776(3) 0.9584(2) 0.0480(9) Uani 1 1 d .
O4 O 0.1930(2) 0.0523(4) 0.6442(2) 0.0519(9) Uani 1 1 d .
N1 N 0.3070(3) 0.2884(3) 0.5743(3) 0.0354(9) Uani 1 1 d .
N2 N 0.7754(3) 0.2518(4) 0.8742(3) 0.0396(9) Uani 1 1 d .
C1 C 0.3886(3) 0.1864(4) 0.5852(3) 0.0288(9) Uani 1 1 d .
C2 C 0.4904(3) 0.2133(4) 0.6598(3) 0.0278(9) Uani 1 1 d .
C3 C 0.4827(3) 0.2857(4) 0.7463(3) 0.0336(10) Uani 1 1 d .
H3A H 0.4122 0.3261 0.7574 0.040 Uiso 1 1 calc R
C4 C 0.5760(3) 0.3004(4) 0.8172(3) 0.0337(10) Uani 1 1 d .
H4A H 0.5705 0.3488 0.8770 0.040 Uiso 1 1 calc R
C5 C 0.6767(3) 0.2422(4) 0.7977(3) 0.0320(10) Uani 1 1 d .
C6 C 0.6879(3) 0.1706(4) 0.7118(3) 0.0334(10) Uani 1 1 d .
H6A H 0.7592 0.1330 0.7004 0.040 Uiso 1 1 calc R
C7 C 0.5936(3) 0.1543(4) 0.6427(3) 0.0312(9) Uani 1 1 d .
H7A H 0.5991 0.1033 0.5839 0.037 Uiso 1 1 calc R
C8 C 0.1932(3) 0.2554(5) 0.5204(3) 0.0421(12) Uani 1 1 d .
C9 C 0.1996(4) 0.2700(6) 0.4116(3) 0.0573(14) Uani 1 1 d .
H9A H 0.1241 0.2510 0.3747 0.069 Uiso 1 1 calc R
H9B H 0.2537 0.2002 0.3910 0.069 Uiso 1 1 calc R
C10 C 0.2381(5) 0.4182(7) 0.3876(4) 0.0769(18) Uani 1 1 d .
H10A H 0.1785 0.4865 0.3997 0.092 Uiso 1 1 calc R
H10B H 0.2482 0.4232 0.3171 0.092 Uiso 1 1 calc R
C11 C 0.3508(4) 0.4589(6) 0.4505(3) 0.0567(14) Uani 1 1 d .
H11A H 0.4137 0.4037 0.4287 0.068 Uiso 1 1 calc R
H11B H 0.3666 0.5597 0.4405 0.068 Uiso 1 1 calc R
C12 C 0.3456(4) 0.4322(4) 0.5581(3) 0.0417(11) Uani 1 1 d .
H12A H 0.4217 0.4465 0.5952 0.050 Uiso 1 1 calc R
H12B H 0.2929 0.5001 0.5831 0.050 Uiso 1 1 calc R
C13 C 0.1044(4) 0.3541(6) 0.5562(3) 0.0527(13) Uani 1 1 d .
H13A H 0.1349 0.4510 0.5585 0.063 Uiso 1 1 calc R
H13B H 0.0357 0.3529 0.5072 0.063 Uiso 1 1 calc R
C14 C 0.0702(4) 0.3195(6) 0.6545(3) 0.0551(13) Uani 1 1 d .
H14A H 0.0168 0.3917 0.6729 0.066 Uiso 1 1 calc R
H14B H 0.1380 0.3204 0.7044 0.066 Uiso 1 1 calc R
C15 C 0.0141(4) 0.1757(6) 0.6533(4) 0.0529(13) Uani 1 1 d .
H15A H 0.0065 0.1472 0.7217 0.063 Uiso 1 1 calc R
H15B H -0.0631 0.1821 0.6169 0.063 Uiso 1 1 calc R
C16 C 0.0781(4) 0.0693(5) 0.6078(3) 0.0523(13) Uani 1 1 d .
H16A H 0.0361 -0.0206 0.5922 0.063 Uiso 1 1 calc R
C17 C 0.1614(4) 0.1008(5) 0.5443(3) 0.0496(12) Uani 1 1 d .
H17A H 0.1692 0.0303 0.4914 0.060 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
C16 O4 C17 60.1(3)
C1 N1 C12 116.6(3)
C1 N1 C8 119.4(3)
C12 N1 C8 113.8(3)
O3 N2 O2 124.2(3)
O3 N2 C5 118.7(4)
O2 N2 C5 117.1(4)
O1 C1 N1 124.3(3)
O1 C1 C2 118.7(3)
N1 C1 C2 116.9(3)
C3 C2 C7 119.9(3)
C3 C2 C1 122.2(3)
C7 C2 C1 117.8(3)
C2 C3 C4 121.1(4)
C5 C4 C3 117.6(4)
C4 C5 C6 122.9(3)
C4 C5 N2 118.1(4)
C6 C5 N2 119.0(3)
C5 C6 C7 118.9(3)
C6 C7 C2 119.6(4)
N1 C8 C9 108.4(3)
N1 C8 C13 109.2(3)
C9 C8 C13 112.3(4)
N1 C8 C17 108.9(3)
C9 C8 C17 109.7(4)
C13 C8 C17 108.4(4)
C8 C9 C10 110.5(4)
C9 C10 C11 111.8(4)
C12 C11 C10 111.4(4)
N1 C12 C11 110.9(4)
C14 C13 C8 115.3(4)
C13 C14 C15 111.0(4)
C16 C15 C14 112.3(4)
O4 C16 C17 61.6(3)
O4 C16 C15 117.8(4)
C17 C16 C15 123.6(5)
C16 C17 O4 58.3(3)
C16 C17 C8 121.9(4)
O4 C17 C8 117.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.223(5)
O2 N2 1.228(5)
O3 N2 1.218(5)
O4 C16 1.403(5)
O4 C17 1.449(6)
N1 C1 1.367(5)
N1 C12 1.469(5)
N1 C8 1.491(5)
N2 C5 1.475(5)
C1 C2 1.505(5)
C2 C3 1.385(6)
C2 C7 1.395(5)
C3 C4 1.387(5)
C4 C5 1.375(6)
C5 C6 1.381(6)
C6 C7 1.382(5)
C8 C9 1.508(6)
C8 C13 1.538(6)
C8 C17 1.563(7)
C9 C10 1.532(8)
C10 C11 1.549(7)
C11 C12 1.505(6)
C13 C14 1.490(7)
C14 C15 1.522(7)
C15 C16 1.453(7)
C16 C17 1.429(7)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C12 N1 C1 O1 -132.6(4)
C8 N1 C1 O1 10.5(6)
C12 N1 C1 C2 51.3(5)
C8 N1 C1 C2 -165.6(3)
O1 C1 C2 C3 -141.9(4)
N1 C1 C2 C3 34.4(5)
O1 C1 C2 C7 33.8(5)
N1 C1 C2 C7 -149.9(4)
C7 C2 C3 C4 -0.4(6)
C1 C2 C3 C4 175.2(4)
C2 C3 C4 C5 1.0(6)
C3 C4 C5 C6 -0.3(6)
C3 C4 C5 N2 -177.4(3)
O3 N2 C5 C4 18.0(5)
O2 N2 C5 C4 -163.9(4)
O3 N2 C5 C6 -159.2(4)
O2 N2 C5 C6 18.9(5)
C4 C5 C6 C7 -1.0(6)
N2 C5 C6 C7 176.1(3)
C5 C6 C7 C2 1.6(6)
C3 C2 C7 C6 -1.0(6)
C1 C2 C7 C6 -176.7(3)
C1 N1 C8 C9 -82.8(5)
C12 N1 C8 C9 61.3(5)
C1 N1 C8 C13 154.6(4)
C12 N1 C8 C13 -61.4(5)
C1 N1 C8 C17 36.4(5)
C12 N1 C8 C17 -179.5(3)
N1 C8 C9 C10 -57.6(5)
C13 C8 C9 C10 63.1(5)
C17 C8 C9 C10 -176.4(4)
C8 C9 C10 C11 54.0(6)
C9 C10 C11 C12 -50.3(6)
C1 N1 C12 C11 86.7(4)
C8 N1 C12 C11 -58.4(5)
C10 C11 C12 N1 51.3(5)
N1 C8 C13 C14 -75.8(5)
C9 C8 C13 C14 163.9(4)
C17 C8 C13 C14 42.6(5)
C8 C13 C14 C15 -62.6(5)
C13 C14 C15 C16 47.4(5)
C17 O4 C16 C15 -115.2(5)
C14 C15 C16 O4 53.8(6)
C14 C15 C16 C17 -18.9(6)
C15 C16 C17 O4 106.1(5)
O4 C16 C17 C8 -104.3(4)
C15 C16 C17 C8 1.7(6)
C16 O4 C17 C8 112.5(5)
N1 C8 C17 C16 106.3(4)
C9 C8 C17 C16 -135.2(4)
C13 C8 C17 C16 -12.3(5)
N1 C8 C17 O4 38.4(5)
C9 C8 C17 O4 156.8(4)
C13 C8 C17 O4 -80.3(4)
