#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:03:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180463 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/32/7213253.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213253
loop_
_publ_author_name
'Rigolet, Séverinne'
'Mélot, Jean Marie'
'Vébrel, Joel'
'Chiaroni, Angèle'
'Riche, Claude'
_publ_section_title
;
 The reaction of α- and ω-methylenelactams with nitrones. Influence of
 electronic and geometric factors on the stereoselectivity of their
 1,3-dipolar cycloaddition
;
_journal_issue                   7
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1095
_journal_paper_doi               10.1039/b000129p
_journal_year                    2000
_chemical_formula_sum            'C36 H32 N4 O6'
_chemical_formula_weight         616.66
_chemical_name_systematic
;
3,11-dibenzoyl-6,13dimethyl-7,14-dioxo-2,10-diphenyl-1,9-dioxa-
2,6,10,13-tetraazaspiro[4.2.2.4]tetradecane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                100.95(2)
_cell_angle_beta                 105.61(2)
_cell_angle_gamma                106.37(2)
_cell_formula_units_Z            1
_cell_length_a                   8.932(2)
_cell_length_b                   9.670(3)
_cell_length_c                   10.105(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2
_cell_measurement_theta_min      12.8
_cell_volume                     772.4(4)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius CAD4 diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2974
_diffrn_reflns_theta_max         67.89
_diffrn_reflns_theta_min         4.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.046
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_restrained_S_obs      1.078
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          -0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0730P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1454
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                2080
_reflns_number_total             2797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b000129psup1.cif
_cod_data_source_block           v113
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.2025P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.2025P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        772.4(3)
_cod_database_code               7213253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4904(3) 0.3530(2) 0.4323(2) 0.0537(5) Uani 1 d .
N2 N 0.5074(2) 0.4567(2) 0.3607(2) 0.0564(5) Uani 1 d .
C3 C 0.4975(2) 0.6031(2) 0.4112(2) 0.0496(5) Uani 1 d .
O4 O 0.3360(2) 0.6015(2) 0.3347(2) 0.0642(5) Uani 1 d .
N5 N 0.3572(2) 0.6978(2) 0.2393(2) 0.0465(4) Uani 1 d .
C6 C 0.5188(2) 0.8169(2) 0.3175(2) 0.0461(5) Uani 1 d .
H6 H 0.5119(2) 0.8935(2) 0.3923(2) 0.051 Uiso 1 calc R
C7 C 0.6225(3) 0.7290(2) 0.3823(3) 0.0581(6) Uani 1 d .
H7A H 0.7115(3) 0.7927(2) 0.4706(3) 0.064 Uiso 1 calc R
H7B H 0.6700(3) 0.6876(2) 0.3156(3) 0.064 Uiso 1 calc R
C8 C 0.4900(5) 0.4036(3) 0.2088(3) 0.0911(9) Uani 1 d .
H8A H 0.5044(5) 0.4869(3) 0.1689(3) 0.109 Uiso 1 calc R
H8B H 0.3814(5) 0.3293(3) 0.1568(3) 0.109 Uiso 1 calc R
H8C H 0.5727(5) 0.3599(3) 0.2017(3) 0.109 Uiso 1 calc R
O9 O 0.4733(3) 0.2227(2) 0.3787(2) 0.0846(6) Uani 1 d .
C10 C 0.2147(2) 0.7397(2) 0.2051(2) 0.0448(4) Uani 1 d .
C11 C 0.2257(3) 0.8863(2) 0.2069(2) 0.0543(5) Uani 1 d .
H11 H 0.3289(3) 0.9627(2) 0.2391(2) 0.060 Uiso 1 calc R
C12 C 0.0820(3) 0.9177(3) 0.1605(3) 0.0696(7) Uani 1 d .
H12 H 0.0895(3) 1.0156(3) 0.1603(3) 0.077 Uiso 1 calc R
C13 C -0.0715(3) 0.8072(3) 0.1147(3) 0.0745(7) Uani 1 d .
H13 H -0.1673(3) 0.8299(3) 0.0844(3) 0.082 Uiso 1 calc R
C14 C -0.0821(3) 0.6623(3) 0.1143(3) 0.0705(7) Uani 1 d .
H14 H -0.1858(3) 0.5868(3) 0.0834(3) 0.078 Uiso 1 calc R
C15 C 0.0592(3) 0.6282(2) 0.1590(2) 0.0581(5) Uani 1 d .
H15 H 0.0505(3) 0.5299(2) 0.1584(2) 0.064 Uiso 1 calc R
C16 C 0.5856(2) 0.8860(2) 0.2115(2) 0.0477(5) Uani 1 d .
O17 O 0.5331(2) 0.8158(2) 0.0860(2) 0.0720(5) Uani 1 d .
C18 C 0.7184(2) 1.0367(2) 0.2665(2) 0.0472(5) Uani 1 d .
C19 C 0.7616(3) 1.1050(3) 0.1668(3) 0.0661(6) Uani 1 d .
H19 H 0.7047(3) 1.0576(3) 0.0694(3) 0.073 Uiso 1 calc R
C20 C 0.8875(4) 1.2417(3) 0.2103(3) 0.0894(9) Uani 1 d .
H20 H 0.9159(4) 1.2862(3) 0.1423(3) 0.098 Uiso 1 calc R
C21 C 0.9716(4) 1.3132(3) 0.3537(4) 0.0869(9) Uani 1 d .
H21 H 1.0574(4) 1.4056(3) 0.3827(4) 0.096 Uiso 1 calc R
C22 C 0.9296(3) 1.2487(3) 0.4543(3) 0.0779(8) Uani 1 d .
H22 H 0.9862(3) 1.2977(3) 0.5515(3) 0.086 Uiso 1 calc R
C23 C 0.8026(3) 1.1103(2) 0.4113(2) 0.0605(6) Uani 1 d .
H23 H 0.7739(3) 1.0668(2) 0.4796(2) 0.067 Uiso 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O9 C1 N2 122.3(2) . .
O9 C1 C3 117.1(2) . 2_666
N2 C1 C3 120.5(2) . 2_666
C1 N2 C3 123.2(2) . .
C1 N2 C8 116.8(2) . .
C3 N2 C8 117.9(2) . .
O4 C3 N2 109.0(2) . .
O4 C3 C1 103.4(2) . 2_666
N2 C3 C1 114.7(2) . 2_666
O4 C3 C7 106.00(14) . .
N2 C3 C7 112.8(2) . .
C1 C3 C7 110.1(2) 2_666 .
C3 O4 N5 107.52(14) . .
C10 N5 C6 118.1(2) . .
C10 N5 O4 106.85(14) . .
C6 N5 O4 104.74(13) . .
N5 C6 C7 101.72(15) . .
N5 C6 C16 109.4(2) . .
C7 C6 C16 111.1(2) . .
C6 C7 C3 103.9(2) . .
C15 C10 C11 119.2(2) . .
C15 C10 N5 118.5(2) . .
C11 C10 N5 122.1(2) . .
C12 C11 C10 119.5(2) . .
C13 C12 C11 121.2(2) . .
C12 C13 C14 119.2(2) . .
C15 C14 C13 120.6(2) . .
C14 C15 C10 120.3(2) . .
O17 C16 C18 121.3(2) . .
O17 C16 C6 119.8(2) . .
C18 C16 C6 118.9(2) . .
C19 C18 C23 118.8(2) . .
C19 C18 C16 117.6(2) . .
C23 C18 C16 123.5(2) . .
C20 C19 C18 120.7(2) . .
C19 C20 C21 120.2(2) . .
C22 C21 C20 120.2(2) . .
C21 C22 C23 120.0(3) . .
C18 C23 C22 120.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O9 1.221(3) .
C1 N2 1.342(3) .
C1 C3 1.524(3) 2_666
N2 C3 1.447(3) .
N2 C8 1.474(3) .
C3 O4 1.436(2) .
C3 C1 1.524(3) 2_666
C3 C7 1.535(3) .
O4 N5 1.473(2) .
N5 C10 1.418(2) .
N5 C6 1.462(2) .
C6 C7 1.530(3) .
C6 C16 1.530(3) .
C10 C15 1.388(3) .
C10 C11 1.389(3) .
C11 C12 1.382(3) .
C12 C13 1.372(4) .
C13 C14 1.376(4) .
C14 C15 1.375(3) .
C16 O17 1.210(2) .
C16 C18 1.484(3) .
C18 C19 1.385(3) .
C18 C23 1.386(3) .
C19 C20 1.372(4) .
C20 C21 1.373(4) .
C21 C22 1.370(4) .
C22 C23 1.388(3) .
