#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:01:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180461 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/30/7213006.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_7213006
loop_
_publ_author_name
'Ziessel, Raymond'
'Ulrich, Gilles'
'Lawson, Raphael C.'
'Echegoyen, Luis'
_publ_section_title
;
 Oligopyridine bis(nitronyl nitroxides): synthesis, structures,
 electrochemical, magnetic and electronic properties
;
_journal_issue                   7
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1435
_journal_paper_doi               10.1039/a810044f
_journal_volume                  9
_journal_year                    1999
_chemical_formula_moiety         'C19 H27 N5 O4'
_chemical_formula_sum            'C19 H27 N5 O4'
_chemical_formula_weight         389.46
_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'
_cell_angle_alpha                90
_cell_angle_beta                 103.30(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.334(5)
_cell_length_b                   10.316(3)
_cell_length_c                   11.990(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      19.5
_cell_volume                     1966.1(10)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1994)
_computing_data_collection       'Philips/PW1100/16 software 1976'
_computing_data_reduction        'pwredu, local program'
_computing_publication_material  BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990)
_computing_structure_refinement  LSFM_MolEN_(Fair,_1990)
_computing_structure_solution    Direct_methods_(SIR,_Burla_et_al.,_1989)
_diffrn_ambient_temperature      173
_diffrn_measurement_device_type  Philips_PW1100
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_sigmaI/netI    0.333
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2490
_diffrn_reflns_theta_max         52.07
_diffrn_reflns_theta_min         3.0
_diffrn_source                   xray_tube
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   refdelf_(Walker_&_Stuart,_1983)
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.153
_refine_ls_abs_structure_details ' ?'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.990
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/esd_mean        0.004
_refine_ls_shift/su_max          0.026
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fo²/(σ²(Fo²)+0.0009 Fo⁴)+3.0'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.047
_refine_ls_wR_factor_ref         0.047
_reflns_number_gt                1849
_reflns_number_total             2490
_reflns_threshold_expression     >3.0σ(I)
_cod_data_source_file            810044fsup1.cif
_cod_data_source_block           st566
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '4Fo^2^/(\s^2^(Fo^2^)+0.0009
Fo^4^)+3.0' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4Fo^2^/(\s^2^(Fo^2^)+0.0009 Fo^4^)+3.0'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1966(1)
_cod_database_code               7213006
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
O1 0.95627(9) 0.1543(2) 0.6126(1) 0.0458(9) Uani ? ? O
O2 0.73301(9) -0.0221(2) 0.7349(1) 0.0386(8) Uani ? ? O
O3 0.76826(9) 0.5185(2) 0.8577(1) 0.0414(9) Uani ? ? O
O4 0.51347(9) 0.4212(2) 0.6147(1) 0.0403(9) Uani ? ? O
N1 0.7427(1) 0.2722(2) 0.6902(1) 0.0305(9) Uani ? ? N
N2 0.9123(1) 0.0766(2) 0.6580(1) 0.0325(9) Uani ? ? N
N3 0.8069(1) -0.0047(2) 0.7193(1) 0.0302(9) Uani ? ? N
N4 0.6902(1) 0.5172(2) 0.8109(1) 0.0306(9) Uani ? ? N
N5 0.5692(1) 0.4765(2) 0.6922(1) 0.0309(9) Uani ? ? N
C1 0.7823(1) 0.2098(2) 0.6196(2) 0.030(1) Uani ? ? C
C2 0.7766(1) 0.2445(2) 0.5063(2) 0.033(1) Uani ? ? C
C3 0.7252(1) 0.3462(2) 0.4614(2) 0.038(1) Uani ? ? C
C4 0.6824(1) 0.4100(2) 0.5313(2) 0.038(1) Uani ? ? C
C5 0.6939(1) 0.3718(2) 0.6442(2) 0.031(1) Uani ? ? C
C6 0.8331(1) 0.0968(2) 0.6667(2) 0.029(1) Uani ? ? C
C7 0.9430(1) -0.0564(2) 0.6966(2) 0.036(1) Uani ? ? C
C8 0.8782(1) -0.0953(2) 0.7680(2) 0.033(1) Uani ? ? C
C9 0.9344(2) -0.1362(3) 0.5877(2) 0.059(1) Uani ? ? C
C10 1.0337(2) -0.0511(3) 0.7626(3) 0.055(2) Uani ? ? C
C11 0.8487(1) -0.2335(3) 0.7551(2) 0.049(1) Uani ? ? C
C12 0.9063(2) -0.0597(3) 0.8944(2) 0.055(2) Uani ? ? C
C13 0.6521(1) 0.4490(2) 0.7191(2) 0.030(1) Uani ? ? C
C14 0.6268(1) 0.5905(2) 0.8609(2) 0.033(1) Uani ? ? C
C15 0.5515(1) 0.5950(2) 0.7554(2) 0.032(1) Uani ? ? C
C16 0.6100(1) 0.5083(3) 0.9579(2) 0.040(1) Uani ? ? C
C17 0.6608(1) 0.7218(3) 0.9046(2) 0.045(1) Uani ? ? C
C18 0.4655(1) 0.5888(3) 0.7812(2) 0.042(1) Uani ? ? C
C19 0.5556(2) 0.7076(2) 0.6743(2) 0.045(1) Uani ? ? C
H1 0.8076 0.1989 0.4607 0.0428 Uiso calc C2 H
H2 0.7194 0.3720 0.3839 0.0494 Uiso calc C3 H
H3 0.6454 0.4794 0.5022 0.0494 Uiso calc C4 H
H4 0.9532 -0.2222 0.6072 0.0748 Uiso calc C9 H
H5 0.8771 -0.1378 0.5472 0.0748 Uiso calc C9 H
H6 0.9676 -0.0984 0.5408 0.0748 Uiso calc C9 H
H7 1.0524 -0.1359 0.7866 0.0785 Uiso calc C10 H
H8 1.0675 -0.0169 0.7148 0.0785 Uiso calc C10 H
H9 1.0382 0.0030 0.8279 0.0785 Uiso calc C10 H
H10 0.8944 -0.2896 0.7862 0.0653 Uiso calc C11 H
H11 0.8052 -0.2457 0.7946 0.0653 Uiso calc C11 H
H12 0.8280 -0.2526 0.6761 0.0653 Uiso calc C11 H
H13 0.8644 -0.0857 0.9332 0.0755 Uiso calc C12 H
H14 0.9577 -0.1025 0.9271 0.0755 Uiso calc C12 H
H15 0.9142 0.0314 0.9016 0.0755 Uiso calc C12 H
H16 0.5702 0.5508 0.9919 0.0541 Uiso calc C16 H
H17 0.5882 0.4265 0.9287 0.0541 Uiso calc C16 H
H18 0.6609 0.4959 1.0138 0.0541 Uiso calc C16 H
H19 0.6202 0.7662 0.9355 0.0583 Uiso calc C17 H
H20 0.7109 0.7109 0.9624 0.0583 Uiso calc C17 H
H21 0.6728 0.7708 0.8431 0.0583 Uiso calc C17 H
H22 0.4562 0.6650 0.8211 0.0556 Uiso calc C18 H
H23 0.4239 0.5827 0.7115 0.0556 Uiso calc C18 H
H24 0.4622 0.5150 0.8273 0.0556 Uiso calc C18 H
H25 0.5449 0.7866 0.7091 0.0593 Uiso calc C19 H
H26 0.6100 0.7108 0.6586 0.0593 Uiso calc C19 H
H27 0.5146 0.6956 0.6048 0.0593 Uiso calc C19 H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1
H 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1
N 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1
O 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 3 2
6 -1 -4
-5 -2 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 115.8(2)
O1 N2 C6 125.8(2)
O1 N2 C7 121.6(2)
C6 N2 C7 112.3(2)
O2 N3 C6 126.4(2)
O2 N3 C8 122.0(2)
C6 N3 C8 111.5(2)
O3 N4 C13 126.9(2)
O3 N4 C14 122.0(2)
C13 N4 C14 111.0(2)
O4 N5 C13 126.1(2)
O4 N5 C15 122.9(2)
C13 N5 C15 110.6(2)
N1 C1 C2 124.1(2)
N1 C1 C6 116.8(2)
C2 C1 C6 119.1(2)
C1 C2 C3 118.6(2)
C2 C3 C4 118.4(2)
C3 C4 C5 119.2(2)
N1 C5 C4 123.8(2)
N1 C5 C13 118.5(2)
C4 C5 C13 117.7(2)
N2 C6 N3 109.5(2)
N2 C6 C1 124.4(2)
N3 C6 C1 126.1(2)
N2 C7 C8 100.6(2)
N2 C7 C9 105.8(2)
N2 C7 C10 110.3(2)
C8 C7 C9 113.0(2)
C8 C7 C10 115.4(2)
C9 C7 C10 110.8(2)
N3 C8 C7 100.9(2)
N3 C8 C11 110.4(2)
N3 C8 C12 105.4(2)
C7 C8 C11 115.4(2)
C7 C8 C12 113.4(2)
C11 C8 C12 110.4(2)
N4 C13 N5 109.7(2)
N4 C13 C5 126.3(2)
N5 C13 C5 123.2(2)
N4 C14 C15 100.3(2)
N4 C14 C16 106.6(2)
N4 C14 C17 110.7(2)
C15 C14 C16 113.2(2)
C15 C14 C17 114.6(2)
C16 C14 C17 110.7(2)
N5 C15 C14 100.3(2)
N5 C15 C18 111.5(2)
N5 C15 C19 104.8(2)
C14 C15 C18 115.7(2)
C14 C15 C19 113.5(2)
C18 C15 C19 110.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.278(3)
O2 N3 1.277(2)
O3 N4 1.269(2)
O4 N5 1.277(2)
N1 C1 1.342(3)
N1 C5 1.339(3)
N2 C6 1.338(3)
N2 C7 1.497(3)
N3 C6 1.342(3)
N3 C8 1.503(3)
N4 C13 1.335(3)
N4 C14 1.513(3)
N5 C13 1.347(3)
N5 C15 1.501(3)
C1 C2 1.387(3)
C1 C6 1.467(3)
C2 C3 1.374(3)
C3 C4 1.376(4)
C4 C5 1.380(3)
C5 C13 1.479(3)
C7 C8 1.560(3)
C7 C9 1.522(4)
C7 C10 1.512(3)
C8 C11 1.501(3)
C8 C12 1.523(3)
C14 C15 1.549(3)
C14 C16 1.514(3)
C14 C17 1.512(3)
C15 C18 1.507(3)
C15 C19 1.527(3)
