#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:10:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179560 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/29/4502944.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_4502944
loop_
_publ_author_name
'Mostovich, Evgeny A.'
'Borozdina, Yulia'
'Enkelmann, Volker'
'Remović-Langer, Katarina'
'Wolf, Bernd'
'Lang, Michael'
'Baumgarten, Martin'
_publ_section_title
;
 Planar Biphenyl-Bridged Biradicals as Building Blocks for the Design of
 Quantum Magnets
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              54
_journal_paper_doi               10.1021/cg201224g
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C13 H16 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O2'
_chemical_formula_weight         232.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-02-26
_audit_creation_method           CRYSTALS_ver_12.39
_cell_angle_alpha                90
_cell_angle_beta                 112.8641(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.26101(5)
_cell_length_b                   11.1001(5)
_cell_length_c                   11.4935(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1206.23(8)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21102
_diffrn_reflns_theta_full        25.075
_diffrn_reflns_theta_max         29.500
_diffrn_reflns_theta_min         4.146
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8569
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.004403
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 -0.133E-01 -1.85 -1.20 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0571
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0571
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1906
_reflns_number_total             3336
_reflns_threshold_expression     I>2.00u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          1.859(2)
_oxford_structure_analysis_title 'Meam-35 Dimer 120K 02-07'
_cod_data_source_file            cg201224g_si_001.cif
_cod_data_source_block           baum2oh
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1206.17(10)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4502944
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.14877(8) 0.12197(7) 0.08292(9) 0.0288 1.0000 Uani .
O2 O 0.60806(7) -0.00362(7) 0.17985(7) 0.0225 1.0000 Uani .
N1 N 0.25785(9) 0.05623(8) 0.11215(8) 0.0190 1.0000 Uani .
N2 N 0.47941(8) -0.00122(8) 0.16586(7) 0.0158 1.0000 Uani .
C1 C 0.48345(10) 0.43889(8) 0.01790(9) 0.0146 1.0000 Uani .
C2 C 0.34891(10) 0.38697(10) -0.04389(10) 0.0195 1.0000 Uani .
C3 C 0.31802(11) 0.27509(9) -0.01191(9) 0.0181 1.0000 Uani .
C4 C 0.42106(10) 0.20791(9) 0.08329(9) 0.0150 1.0000 Uani .
C5 C 0.55508(9) 0.25818(10) 0.14560(10) 0.0179 1.0000 Uani .
C6 C 0.58472(10) 0.37296(9) 0.11517(9) 0.0160 1.0000 Uani .
C7 C 0.38661(10) 0.09067(9) 0.11788(9) 0.0176 1.0000 Uani .
C8 C 0.25371(11) -0.07679(10) 0.13520(10) 0.0202 1.0000 Uani .
C9 C 0.15460(13) -0.10352(12) 0.19970(12) 0.0331 1.0000 Uani .
C10 C 0.20215(11) -0.13619(11) 0.00496(11) 0.0247 1.0000 Uani .
C11 C 0.41343(11) -0.09981(10) 0.21539(10) 0.0187 1.0000 Uani .
C12 C 0.45554(13) -0.07325(11) 0.35593(10) 0.0265 1.0000 Uani .
C13 C 0.46797(12) -0.22248(10) 0.19758(11) 0.0258 1.0000 Uani .
H21 H 0.2782 0.4308 -0.1092 0.0238 1.0000 Uiso R
H31 H 0.2267 0.2412 -0.0545 0.0206 1.0000 Uiso R
H51 H 0.6261 0.2126 0.2088 0.0229 1.0000 Uiso R
H61 H 0.6749 0.4078 0.1606 0.0236 1.0000 Uiso R
H91 H 0.1535 -0.1878 0.2138 0.0410 1.0000 Uiso R
H92 H 0.1862 -0.0624 0.2783 0.0410 1.0000 Uiso R
H93 H 0.0619 -0.0772 0.1482 0.0410 1.0000 Uiso R
H101 H 0.1970 -0.2209 0.0139 0.0314 1.0000 Uiso R
H102 H 0.2669 -0.1185 -0.0334 0.0314 1.0000 Uiso R
H103 H 0.1112 -0.1061 -0.0465 0.0314 1.0000 Uiso R
H121 H 0.4165 -0.1333 0.3918 0.0339 1.0000 Uiso R
H122 H 0.5556 -0.0732 0.3981 0.0339 1.0000 Uiso R
H123 H 0.4195 0.0035 0.3650 0.0339 1.0000 Uiso R
H131 H 0.4251 -0.2832 0.2290 0.0367 1.0000 Uiso R
H132 H 0.5676 -0.2246 0.2428 0.0367 1.0000 Uiso R
H133 H 0.4463 -0.2363 0.1105 0.0367 1.0000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 . N1 C7 126.56(9) yes
O1 . N1 C8 121.98(8) yes
C7 . N1 C8 111.28(8) yes
O2 . N2 C7 126.82(9) yes
O2 . N2 C11 122.33(8) yes
C7 . N2 C11 110.57(8) yes
C1 2_665 C1 C2 121.07(11) yes
C1 2_665 C1 C6 121.09(11) yes
C2 . C1 C6 117.84(9) yes
C1 . C2 C3 121.39(10) yes
C1 . C2 H21 119.176 no
C3 . C2 H21 119.438 no
C2 . C3 C4 120.59(9) yes
C2 . C3 H31 120.419 no
C4 . C3 H31 118.986 no
C3 . C4 C5 118.73(10) yes
C3 . C4 C7 120.15(9) yes
C5 . C4 C7 121.10(9) yes
C4 . C5 C6 120.46(9) yes
C4 . C5 H51 119.276 no
C6 . C5 H51 120.267 no
C1 . C6 C5 120.94(9) yes
C1 . C6 H61 119.245 no
C5 . C6 H61 119.816 no
C4 . C7 N2 125.50(9) yes
C4 . C7 N1 125.48(9) yes
N2 . C7 N1 108.98(9) yes
N1 . C8 C9 110.59(9) yes
N1 . C8 C10 105.87(9) yes
C9 . C8 C10 110.77(9) yes
N1 . C8 C11 99.79(8) yes
C9 . C8 C11 115.71(9) yes
C10 . C8 C11 113.12(9) yes
C8 . C9 H91 109.506 no
C8 . C9 H92 109.170 no
H91 . C9 H92 109.476 no
C8 . C9 H93 109.724 no
H91 . C9 H93 109.476 no
H92 . C9 H93 109.475 no
C8 . C10 H101 109.467 no
C8 . C10 H102 109.066 no
H101 . C10 H102 109.476 no
C8 . C10 H103 109.866 no
H101 . C10 H103 109.476 no
H102 . C10 H103 109.475 no
C8 . C11 N2 100.42(8) yes
C8 . C11 C12 113.18(9) yes
N2 . C11 C12 105.92(9) yes
C8 . C11 C13 115.22(9) yes
N2 . C11 C13 110.91(9) yes
C12 . C11 C13 110.37(9) yes
C11 . C12 H121 109.212 no
C11 . C12 H122 110.148 no
H121 . C12 H122 109.476 no
C11 . C12 H123 109.038 no
H121 . C12 H123 109.475 no
H122 . C12 H123 109.476 no
C11 . C13 H131 109.669 no
C11 . C13 H132 108.871 no
H131 . C13 H132 109.475 no
C11 . C13 H133 109.859 no
H131 . C13 H133 109.475 no
H132 . C13 H133 109.477 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.2672(11) yes
O2 N2 . 1.2667(10) yes
N1 C7 . 1.3522(13) yes
N1 C8 . 1.5036(14) yes
N2 C7 . 1.3576(12) yes
N2 C11 . 1.5098(13) yes
C1 C1 2_665 1.4947(19) yes
C1 C2 . 1.4073(13) yes
C1 C6 . 1.4008(13) yes
C2 C3 . 1.3669(15) yes
C2 H21 . 0.950 no
C3 C4 . 1.4043(13) yes
C3 H31 . 0.950 no
C4 C5 . 1.3965(12) yes
C4 C7 . 1.4442(14) yes
C5 C6 . 1.3859(15) yes
C5 H51 . 0.950 no
C6 H61 . 0.950 no
C8 C9 . 1.5025(15) yes
C8 C10 . 1.5297(16) yes
C8 C11 . 1.5578(14) yes
C9 H91 . 0.950 no
C9 H92 . 0.950 no
C9 H93 . 0.950 no
C10 H101 . 0.950 no
C10 H102 . 0.950 no
C10 H103 . 0.950 no
C11 C12 . 1.5297(15) yes
C11 C13 . 1.5160(14) yes
C12 H121 . 0.950 no
C12 H122 . 0.950 no
C12 H123 . 0.950 no
C13 H131 . 0.950 no
C13 H132 . 0.950 no
C13 H133 . 0.950 no
