#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:01:59 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178930 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/59/4115939.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_4115939
loop_
_publ_author_name
'Natia L. Frank'
'Rodolphe Clérac'
'Jean-Pascal Sutter'
'Nathalie Daro'
'Olivier Kahn'
'Claude Coulon'
'Michael T. Green'
'Stéphane Golhen'
'Lahcène Ouahab'
_publ_section_title
;
 Synthesis, Crystal Structure, Magnetic, and Electron Paramagnetic
 Resonance Properties of a Spiroconjugated Biradical. Evidence for
 Spiroconjugation Exchange Pathway
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2053
_journal_page_last               2061
_journal_paper_doi               10.1021/ja993071a
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C35 H46 N4 O4'
_chemical_formula_weight         586.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 117.482(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.861(10)
_cell_length_b                   12.129(3)
_cell_length_c                   12.258(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.088
_cell_measurement_theta_min      4.707
_cell_volume                     3279(2)
_computing_cell_refinement       MolEN
_computing_data_collection       'Enraf Nonius CAD4'
_computing_data_reduction        MolEN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.471
_diffrn_measured_fraction_theta_max 0.471
_diffrn_measurement_device_type  'Enraf nonius'
_diffrn_measurement_method       θ-2θ
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.1424
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3235
_diffrn_reflns_theta_full        25.92
_diffrn_reflns_theta_max         25.92
_diffrn_reflns_theta_min         1.85
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.999522
_exptl_absorpt_correction_T_min  0.949579
_exptl_absorpt_correction_type   '\y scan'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.2025
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0701P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                1367
_reflns_number_total             3161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja993071a.cif
_cod_data_source_block           abs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.0000P] 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^)+(0.0701P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4115939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_calc_flag
_atom_site_refinement_flags
C1 C 0.5000 0.0743(4) 0.2500 0.0325(12) Uani 1 d S
O1 O 0.28907(11) 0.4403(2) -0.1109(2) 0.0534(8) Uani 1 d .
O2 O 0.46468(11) 0.3132(2) -0.1123(2) 0.0515(8) Uani 1 d .
N1 N 0.33209(13) 0.4238(2) -0.1408(3) 0.0407(8) Uani 1 d .
N2 N 0.41558(12) 0.3657(2) -0.1388(2) 0.0368(7) Uani 1 d .
C2 C 0.44423(14) 0.1411(3) 0.1647(3) 0.0294(8) Uani 1 d .
C3 C 0.44140(15) 0.2241(3) 0.0843(3) 0.0305(8) Uani 1 d .
C4 C 0.38505(14) 0.2685(3) 0.0045(3) 0.0300(8) Uani 1 d .
C5 C 0.33264(16) 0.2289(3) 0.0072(3) 0.0357(9) Uani 1 d .
C6 C 0.33625(15) 0.1454(3) 0.0872(3) 0.0375(9) Uani 1 d .
C7 C 0.39246(15) 0.1024(3) 0.1661(3) 0.0315(8) Uani 1 d .
C8 C 0.40506(16) 0.0075(3) 0.2551(3) 0.0443(10) Uani 1 d .
C9 C 0.47453(17) 0.0065(4) 0.3236(4) 0.0454(11) Uani 1 d .
C10 C 0.3807(4) -0.0996(5) 0.1818(7) 0.103(3) Uani 1 d .
C11 C 0.3773(3) 0.0253(7) 0.3402(6) 0.096(2) Uani 1 d .
C12 C 0.37842(14) 0.3521(3) -0.0871(3) 0.0320(8) Uani 1 d .
C13 C 0.33003(18) 0.4770(3) -0.2522(4) 0.0547(12) Uani 1 d .
C14 C 0.2836(2) 0.4081(7) -0.3628(4) 0.088(2) Uani 1 d .
C15 C 0.3091(4) 0.5954(6) -0.2591(9) 0.102(3) Uani 1 d .
C16 C 0.39602(16) 0.4601(3) -0.2291(3) 0.0447(10) Uani 1 d .
C17 C 0.4382(2) 0.5555(4) -0.1621(5) 0.0678(14) Uani 1 d .
C18 C 0.4036(3) 0.4258(5) -0.3409(4) 0.0676(14) Uani 1 d .
H1 H 0.4911(15) -0.067(3) 0.341(3) 0.046(11) Uiso 1 d .
H2 H 0.2990(14) 0.121(3) 0.090(3) 0.045(10) Uiso 1 d .
H3 H 0.4770(12) 0.248(2) 0.084(2) 0.016(8) Uiso 1 d .
H4 H 0.2941(14) 0.256(2) -0.051(3) 0.036(9) Uiso 1 d .
H5 H 0.339(2) 0.640(5) -0.162(5) 0.13(2) Uiso 1 d .
H6 H 0.375(2) 0.354(4) -0.390(4) 0.084(15) Uiso 1 d .
H7 H 0.447(3) 0.407(4) -0.317(5) 0.12(2) Uiso 1 d .
H8 H 0.4255(19) 0.624(4) -0.214(4) 0.080(14) Uiso 1 d .
H9 H 0.3899(19) 0.489(4) -0.391(4) 0.076(15) Uiso 1 d .
H10 H 0.480(2) 0.530(4) -0.135(5) 0.108(19) Uiso 1 d .
H11 H 0.3961(17) 0.102(3) 0.385(3) 0.052(14) Uiso 1 d .
H12 H 0.390(2) -0.032(4) 0.393(5) 0.097(18) Uiso 1 d .
H13 H 0.428(2) 0.586(4) -0.088(5) 0.104(18) Uiso 1 d .
H14 H 0.389(2) -0.153(4) 0.242(5) 0.100(18) Uiso 1 d .
H15 H 0.383(4) -0.116(6) 0.112(7) 0.18(4) Uiso 1 d .
H16 H 0.283(2) 0.439(4) -0.431(5) 0.102(18) Uiso 1 d .
H17 H 0.338(3) -0.094(4) 0.143(6) 0.12(2) Uiso 1 d .
H18 H 0.313(2) 0.618(4) -0.316(4) 0.072(17) Uiso 1 d .
H19 H 0.242(2) 0.407(4) -0.359(4) 0.12(2) Uiso 1 d .
H20 H 0.295(2) 0.319(5) -0.350(5) 0.14(3) Uiso 1 d .
H21 H 0.337(3) 0.042(4) 0.308(5) 0.11(2) Uiso 1 d .
H22 H 0.4876(18) 0.041(3) 0.410(4) 0.075(13) Uiso 1 d .
H23 H 0.267(3) 0.593(5) -0.271(6) 0.16(3) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C2 116.0(4) 2_655 .
C2 C1 C9 111.56(19) 2_655 .
C2 C1 C9 101.1(2) . .
C2 C1 C9 101.1(2) 2_655 2_655
C2 C1 C9 111.56(19) . 2_655
C9 C1 C9 116.1(5) . 2_655
O1 N1 C12 126.3(3) . .
O1 N1 C13 120.6(3) . .
C12 N1 C13 112.8(3) . .
O2 N2 C12 126.8(3) . .
O2 N2 C16 120.7(3) . .
C12 N2 C16 112.3(3) . .
C7 C2 C3 121.0(3) . .
C7 C2 C1 111.7(3) . .
C3 C2 C1 127.1(3) . .
C2 C3 C4 118.9(3) . .
C3 C4 C5 119.6(3) . .
C3 C4 C12 121.8(3) . .
C5 C4 C12 118.5(3) . .
C6 C5 C4 120.7(3) . .
C5 C6 C7 119.1(3) . .
C2 C7 C6 120.7(3) . .
C2 C7 C8 112.6(3) . .
C6 C7 C8 126.6(3) . .
C11 C8 C7 112.4(4) . .
C11 C8 C9 112.4(4) . .
C7 C8 C9 101.9(3) . .
C11 C8 C10 110.0(6) . .
C7 C8 C10 109.1(4) . .
C9 C8 C10 110.8(5) . .
C8 C9 C1 109.6(3) . .
N1 C12 N2 107.9(3) . .
N1 C12 C4 126.1(3) . .
N2 C12 C4 125.8(3) . .
N1 C13 C15 109.1(4) . .
N1 C13 C16 100.9(3) . .
C15 C13 C16 116.3(4) . .
N1 C13 C14 105.3(4) . .
C15 C13 C14 111.3(5) . .
C16 C13 C14 112.7(4) . .
N2 C16 C17 105.8(3) . .
N2 C16 C18 108.8(4) . .
C17 C16 C18 110.6(4) . .
N2 C16 C13 101.0(3) . .
C17 C16 C13 114.0(4) . .
C18 C16 C13 115.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.527(4) 2_655
C1 C2 1.527(4) .
C1 C9 1.555(4) .
C1 C9 1.555(4) 2_655
O1 N1 1.296(4) .
O2 N2 1.279(3) .
N1 C12 1.348(4) .
N1 C13 1.490(4) .
N2 C12 1.349(4) .
N2 C16 1.508(4) .
C2 C7 1.377(4) .
C2 C3 1.388(5) .
C3 C4 1.394(4) .
C4 C5 1.403(4) .
C4 C12 1.465(4) .
C5 C6 1.384(5) .
C6 C7 1.383(4) .
C7 C8 1.516(5) .
C8 C11 1.508(7) .
C8 C9 1.533(5) .
C8 C10 1.536(7) .
C13 C15 1.516(7) .
C13 C16 1.544(5) .
C13 C14 1.557(7) .
C16 C17 1.523(6) .
C16 C18 1.525(6) .
