#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:47:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180518 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/87/7218748.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_7218748
loop_
_publ_author_name
'Ravat, Prince'
'Baumgarten, Martin'
_publ_section_title
;
 "Tschitschibabin type biradicals": benzenoid or quinoid?
;
_journal_issue                   2
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              983
_journal_page_last               991
_journal_paper_doi               10.1039/c4cp03522d
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C26 H30 N2 O2'
_chemical_formula_sum            'C26 H30 N2 O2'
_chemical_formula_weight         402.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-02-12
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 94.802(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8404(2)
_cell_length_b                   8.9886(3)
_cell_length_c                   13.3460(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1056.79(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.055
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13179
_diffrn_reflns_theta_full        30.038
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_min         3.499
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0718
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.0016420
_refine_ls_shift/su_mean         0.0004057
_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: 
 1.40 0.609 0.891 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0643
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0574
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2464
_reflns_number_total             3090
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            c4cp03522d2.cif
_cod_data_source_block           ravterp_120
_cod_depositor_comments
'Adding full bibliography for 7218748--7218750.cif.'
_cod_original_sg_symbol_H-M      'P 1 21/a 1 '
_cod_database_code               7218748
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 1.06551(11) 0.66135(12) 0.59817(7) 0.0274 1.0000 Uani .
N1 N 1.08158(11) 0.55079(12) 0.65985(7) 0.0188 1.0000 Uani .
C5 C 0.72396(13) 0.61083(14) 0.77868(9) 0.0186 1.0000 Uani .
C2 C 0.51601(14) 0.62856(13) 0.94414(8) 0.0189 1.0000 Uani .
C9 C 0.87671(14) 0.44248(15) 0.88271(9) 0.0225 1.0000 Uani .
C3 C 0.61929(13) 0.51187(13) 0.93490(8) 0.0175 1.0000 Uani .
C1 C 0.60067(14) 0.38323(13) 0.99251(9) 0.0190 1.0000 Uani .
C6 C 0.83616(13) 0.61845(14) 0.71240(9) 0.0191 1.0000 Uani .
C7 C 0.97123(13) 0.53696(13) 0.73001(8) 0.0178 1.0000 Uani .
C4 C 0.74089(13) 0.52228(13) 0.86567(8) 0.0177 1.0000 Uani .
C8 C 0.99015(14) 0.44802(15) 0.81686(9) 0.0234 1.0000 Uani .
C11 C 1.33087(14) 0.46577(15) 0.73997(10) 0.0238 1.0000 Uani .
C12 C 1.15436(16) 0.28600(15) 0.64059(11) 0.0287 1.0000 Uani .
C10 C 1.21280(13) 0.44603(14) 0.65006(9) 0.0196 1.0000 Uani .
C13 C 1.28492(17) 0.48789(17) 0.55391(10) 0.0283 1.0000 Uani .
H51 H 0.6332 0.6665 0.7651 0.0249 1.0000 Uiso R
H21 H 0.5259 0.7170 0.9062 0.0255 1.0000 Uiso R
H91 H 0.8913 0.3825 0.9413 0.0301 1.0000 Uiso R
H11 H 0.6693 0.3026 0.9880 0.0258 1.0000 Uiso R
H61 H 0.8217 0.6796 0.6543 0.0254 1.0000 Uiso R
H81 H 1.0805 0.3917 0.8303 0.0304 1.0000 Uiso R
H111 H 1.4136 0.4000 0.7335 0.0317 1.0000 Uiso R
H112 H 1.3665 0.5655 0.7420 0.0317 1.0000 Uiso R
H113 H 1.2853 0.4440 0.8003 0.0317 1.0000 Uiso R
H121 H 1.2372 0.2204 0.6342 0.0393 1.0000 Uiso R
H122 H 1.1055 0.2608 0.6990 0.0393 1.0000 Uiso R
H123 H 1.0841 0.2774 0.5830 0.0393 1.0000 Uiso R
H131 H 1.3683 0.4237 0.5456 0.0375 1.0000 Uiso R
H132 H 1.3195 0.5879 0.5586 0.0375 1.0000 Uiso R
H133 H 1.2120 0.4780 0.4979 0.0375 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . N1 C7 . 116.43(10) yes
O1 . N1 C10 . 118.03(9) yes
C7 . N1 C10 . 125.53(10) yes
C6 . C5 C4 . 121.55(11) yes
C6 . C5 H51 . 119.4 no
C4 . C5 H51 . 119.1 no
C1 2_667 C2 C3 . 121.17(11) yes
C1 2_667 C2 H21 . 119.5 no
C3 . C2 H21 . 119.3 no
C4 . C9 C8 . 122.24(11) yes
C4 . C9 H91 . 118.7 no
C8 . C9 H91 . 119.1 no
C2 . C3 C1 . 117.39(10) yes
C2 . C3 C4 . 121.36(11) yes
C1 . C3 C4 . 121.24(11) yes
C3 . C1 C2 2_667 121.44(11) yes
C3 . C1 H11 . 119.2 no
C2 2_667 C1 H11 . 119.3 no
C5 . C6 C7 . 120.79(11) yes
C5 . C6 H61 . 119.7 no
C7 . C6 H61 . 119.6 no
N1 . C7 C6 . 117.90(10) yes
N1 . C7 C8 . 123.71(10) yes
C6 . C7 C8 . 118.38(10) yes
C3 . C4 C5 . 121.31(10) yes
C3 . C4 C9 . 121.63(10) yes
C5 . C4 C9 . 117.05(10) yes
C7 . C8 C9 . 119.97(11) yes
C7 . C8 H81 . 119.9 no
C9 . C8 H81 . 120.1 no
C10 . C11 H111 . 109.6 no
C10 . C11 H112 . 109.5 no
H111 . C11 H112 . 109.5 no
C10 . C11 H113 . 109.2 no
H111 . C11 H113 . 109.5 no
H112 . C11 H113 . 109.5 no
C10 . C12 H121 . 109.5 no
C10 . C12 H122 . 109.3 no
H121 . C12 H122 . 109.5 no
C10 . C12 H123 . 109.7 no
H121 . C12 H123 . 109.5 no
H122 . C12 H123 . 109.5 no
C11 . C10 C12 . 112.12(11) yes
C11 . C10 N1 . 109.76(10) yes
C12 . C10 N1 . 109.72(10) yes
C11 . C10 C13 . 108.93(10) yes
C12 . C10 C13 . 108.91(11) yes
N1 . C10 C13 . 107.29(10) yes
C10 . C13 H131 . 109.4 no
C10 . C13 H132 . 109.4 no
H131 . C13 H132 . 109.5 no
C10 . C13 H133 . 109.6 no
H131 . C13 H133 . 109.5 no
H132 . C13 H133 . 109.5 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 . 1.2907(14) yes
N1 C7 . 1.4131(14) yes
N1 C10 . 1.5083(15) yes
C5 C6 . 1.3849(16) yes
C5 C4 . 1.4052(16) yes
C5 H51 . 0.950 no
C2 C1 2_667 1.3914(16) yes
C2 C3 . 1.4028(16) yes
C2 H21 . 0.950 no
C9 C4 . 1.4008(16) yes
C9 C8 . 1.3886(17) yes
C9 H91 . 0.950 no
C3 C1 . 1.4059(16) yes
C3 C4 . 1.4779(16) yes
C1 H11 . 0.950 no
C6 C7 . 1.4038(16) yes
C6 H61 . 0.950 no
C7 C8 . 1.4065(16) yes
C8 H81 . 0.950 no
C11 C10 . 1.5333(16) yes
C11 H111 . 0.950 no
C11 H112 . 0.950 no
C11 H113 . 0.950 no
C12 C10 . 1.5300(18) yes
C12 H121 . 0.950 no
C12 H122 . 0.950 no
C12 H123 . 0.950 no
C10 C13 . 1.5270(17) yes
C13 H131 . 0.950 no
C13 H132 . 0.950 no
C13 H133 . 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 H122 C8 125.25(4) 0.950 2.571 3.2148(18) yes
