#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:47:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180518 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/87/7218749.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_7218749
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         'C40 H42 N2 O6'
_chemical_formula_sum            'C40 H42 N2 O6'
_chemical_formula_weight         646.78
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-03-21
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 113.4267(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1306(8)
_cell_length_b                   11.2298(3)
_cell_length_c                   17.6135(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3290.6(2)
_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  0.088
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13979
_diffrn_reflns_theta_full        28.653
_diffrn_reflns_theta_max         28.653
_diffrn_reflns_theta_min         2.728
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.0003641
_refine_ls_shift/su_mean         0.0000642
_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: 
 5.75 4.55 4.88 1.62 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1024
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0934
_reflns_limit_h_max              22
_reflns_limit_h_min              -24
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3411
_reflns_number_total             4234
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            c4cp03522d2.cif
_cod_data_source_block           ravdipyrad
_cod_depositor_comments
'Adding full bibliography for 7218748--7218750.cif.'
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               7218749
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,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
-x,y,-z+1/2
x,-y,z+1/2
-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
N1 N 0.24533(16) 0.9536(2) 0.18086(14) 0.0357 1.0000 Uani .
O1 O 0.45989(11) 1.23163(15) 0.66464(12) 0.0278 1.0000 Uani .
O2 O 0.45899(12) 0.58238(16) 0.66448(11) 0.0300 1.0000 Uani .
O3 O 0.2472(2) 1.0601(2) 0.15709(16) 0.0775 1.0000 Uani .
C1 C 0.47893(15) 0.9064(2) 0.70588(15) 0.0237 1.0000 Uani .
C2 C 0.45867(16) 1.0162(2) 0.66229(16) 0.0254 1.0000 Uani .
C3 C 0.41811(16) 1.0145(2) 0.57631(16) 0.0272 1.0000 Uani .
C4 C 0.39920(16) 0.9076(2) 0.53203(15) 0.0268 1.0000 Uani .
C5 C 0.41786(16) 0.7993(2) 0.57541(15) 0.0259 1.0000 Uani .
C6 C 0.45704(15) 0.7981(2) 0.66196(15) 0.0243 1.0000 Uani .
C7 C 0.47871(16) 0.6881(2) 0.70810(16) 0.0256 1.0000 Uani .
C8 C 0.48109(16) 1.1261(2) 0.70833(17) 0.0266 1.0000 Uani .
C9 C 0.36103(16) 0.9124(2) 0.44060(15) 0.0273 1.0000 Uani .
C10 C 0.37977(17) 1.0041(2) 0.39765(17) 0.0293 1.0000 Uani .
C11 C 0.34301(17) 1.0134(2) 0.31292(17) 0.0310 1.0000 Uani .
C12 C 0.28529(17) 0.9312(2) 0.26713(16) 0.0289 1.0000 Uani .
C13 C 0.26849(17) 0.8341(2) 0.30746(17) 0.0297 1.0000 Uani .
C14 C 0.30576(16) 0.8267(2) 0.39373(16) 0.0291 1.0000 Uani .
C15 C 0.20145(18) 0.8625(3) 0.11527(17) 0.0322 1.0000 Uani .
C16 C 0.1894(2) 0.9180(3) 0.03195(19) 0.0411 1.0000 Uani .
C17 C 0.11995(18) 0.8364(3) 0.11672(19) 0.0387 1.0000 Uani .
C18 C 0.25463(19) 0.7523(3) 0.12860(19) 0.0349 1.0000 Uani .
C19 C 0.52474(19) 1.2827(3) 0.6483(2) 0.0351 1.0000 Uani .
C20 C 0.39577(18) 0.5181(3) 0.6751(2) 0.0361 1.0000 Uani .
H31 H 0.4042 1.0878 0.5468 0.0317 1.0000 Uiso R
H51 H 0.4038 0.7267 0.5453 0.0329 1.0000 Uiso R
H101 H 0.4199 1.0616 0.4282 0.0302 1.0000 Uiso R
H111 H 0.3584 1.0754 0.2847 0.0337 1.0000 Uiso R
H131 H 0.2332 0.7727 0.2766 0.0319 1.0000 Uiso R
H141 H 0.2932 0.7619 0.4217 0.0358 1.0000 Uiso R
H161 H 0.1633 0.8652 -0.0111 0.0684 1.0000 Uiso R
H162 H 0.1577 0.9900 0.0240 0.0684 1.0000 Uiso R
H163 H 0.2403 0.9411 0.0315 0.0684 1.0000 Uiso R
H171 H 0.0920 0.7780 0.0763 0.0585 1.0000 Uiso R
H172 H 0.0895 0.9074 0.1061 0.0585 1.0000 Uiso R
H173 H 0.1272 0.8067 0.1702 0.0585 1.0000 Uiso R
H181 H 0.2285 0.6934 0.0872 0.0567 1.0000 Uiso R
H182 H 0.3046 0.7724 0.1253 0.0567 1.0000 Uiso R
H183 H 0.2658 0.7181 0.1816 0.0567 1.0000 Uiso R
H191 H 0.5065 1.3544 0.6174 0.0604 1.0000 Uiso R
H192 H 0.5688 1.2996 0.6983 0.0604 1.0000 Uiso R
H193 H 0.5407 1.2281 0.6163 0.0604 1.0000 Uiso R
H201 H 0.3861 0.4460 0.6449 0.0585 1.0000 Uiso R
H202 H 0.4105 0.5014 0.7322 0.0585 1.0000 Uiso R
H203 H 0.3484 0.5656 0.6554 0.0585 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
O3 . N1 C12 . 116.7(2) yes
O3 . N1 C15 . 117.4(2) yes
C12 . N1 C15 . 125.9(2) yes
C8 . O1 C19 . 112.7(2) yes
C7 . O2 C20 . 113.9(2) yes
C1 5_656 C1 C2 . 119.84(14) yes
C1 5_656 C1 C6 . 120.46(13) yes
C2 . C1 C6 . 119.7(2) yes
C1 . C2 C3 . 119.1(2) yes
C1 . C2 C8 . 118.9(2) yes
C3 . C2 C8 . 122.0(2) yes
C2 . C3 C4 . 121.6(2) yes
C2 . C3 H31 . 119.4 no
C4 . C3 H31 . 119.0 no
C3 . C4 C5 . 119.2(2) yes
C3 . C4 C9 . 118.7(2) yes
C5 . C4 C9 . 122.1(2) yes
C4 . C5 C6 . 120.5(2) yes
C4 . C5 H51 . 119.1 no
C6 . C5 H51 . 120.4 no
C1 . C6 C5 . 119.9(2) yes
C1 . C6 C7 . 118.3(2) yes
C5 . C6 C7 . 121.8(2) yes
C6 . C7 O2 . 118.0(2) yes
C6 . C7 C7 5_656 121.20(13) yes
O2 . C7 C7 5_656 120.70(13) yes
C2 . C8 O1 . 117.8(2) yes
C2 . C8 C8 5_656 121.21(14) yes
O1 . C8 C8 5_656 120.94(13) yes
C4 . C9 C10 . 120.5(2) yes
C4 . C9 C14 . 122.2(2) yes
C10 . C9 C14 . 117.3(2) yes
C9 . C10 C11 . 121.8(3) yes
C9 . C10 H101 . 119.0 no
C11 . C10 H101 . 119.2 no
C10 . C11 C12 . 120.5(3) yes
C10 . C11 H111 . 120.2 no
C12 . C11 H111 . 119.3 no
N1 . C12 C11 . 116.7(2) yes
N1 . C12 C13 . 124.0(2) yes
C11 . C12 C13 . 119.3(2) yes
C12 . C13 C14 . 119.3(2) yes
C12 . C13 H131 . 120.5 no
C14 . C13 H131 . 120.2 no
C13 . C14 C9 . 121.6(2) yes
C13 . C14 H141 . 119.6 no
C9 . C14 H141 . 118.8 no
N1 . C15 C16 . 106.8(2) yes
N1 . C15 C17 . 109.8(2) yes
C16 . C15 C17 . 109.1(2) yes
N1 . C15 C18 . 108.8(2) yes
C16 . C15 C18 . 108.6(2) yes
C17 . C15 C18 . 113.6(3) yes
C15 . C16 H161 . 110.8 no
C15 . C16 H162 . 109.2 no
H161 . C16 H162 . 109.5 no
C15 . C16 H163 . 110.2 no
H161 . C16 H163 . 110.1 no
H162 . C16 H163 . 106.9 no
C15 . C17 H171 . 110.7 no
C15 . C17 H172 . 109.2 no
H171 . C17 H172 . 109.7 no
C15 . C17 H173 . 109.3 no
H171 . C17 H173 . 108.7 no
H172 . C17 H173 . 109.2 no
C15 . C18 H181 . 110.5 no
C15 . C18 H182 . 110.7 no
H181 . C18 H182 . 108.1 no
C15 . C18 H183 . 110.6 no
H181 . C18 H183 . 108.4 no
H182 . C18 H183 . 108.5 no
O1 . C19 H191 . 109.0 no
O1 . C19 H192 . 110.4 no
H191 . C19 H192 . 109.6 no
O1 . C19 H193 . 109.1 no
H191 . C19 H193 . 108.9 no
H192 . C19 H193 . 109.8 no
O2 . C20 H201 . 109.8 no
O2 . C20 H202 . 109.6 no
H201 . C20 H202 . 109.7 no
O2 . C20 H203 . 108.9 no
H201 . C20 H203 . 109.7 no
H202 . C20 H203 . 109.1 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
N1 O3 . 1.273(3) yes
N1 C12 . 1.422(3) yes
N1 C15 . 1.511(4) yes
O1 C8 . 1.381(3) yes
O1 C19 . 1.436(3) yes
O2 C7 . 1.382(3) yes
O2 C20 . 1.428(3) yes
C1 C1 5_656 1.433(5) yes
C1 C2 . 1.421(3) yes
C1 C6 . 1.411(3) yes
C2 C3 . 1.396(4) yes
C2 C8 . 1.444(3) yes
C3 C4 . 1.398(3) yes
C3 H31 . 0.953 no
C4 C5 . 1.404(3) yes
C4 C9 . 1.480(3) yes
C5 C6 . 1.403(4) yes
C5 H51 . 0.950 no
C6 C7 . 1.444(3) yes
C7 C7 5_656 1.367(5) yes
C8 C8 5_656 1.351(5) yes
C9 C10 . 1.397(4) yes
C9 C14 . 1.398(4) yes
C10 C11 . 1.375(4) yes
C10 H101 . 0.961 no
C11 C12 . 1.388(4) yes
C11 H111 . 0.959 no
C12 C13 . 1.399(4) yes
C13 C14 . 1.399(4) yes
C13 H131 . 0.951 no
C14 H141 . 0.955 no
C15 C16 . 1.528(4) yes
C15 C17 . 1.517(4) yes
C15 C18 . 1.529(4) yes
C16 H161 . 0.930 no
C16 H162 . 0.969 no
C16 H163 . 0.962 no
C17 H171 . 0.952 no
C17 H172 . 0.946 no
C17 H173 . 0.958 no
C18 H181 . 0.959 no
C18 H182 . 0.958 no
C18 H183 . 0.954 no
C19 H191 . 0.955 no
C19 H192 . 0.944 no
C19 H193 . 0.952 no
C20 H201 . 0.945 no
C20 H202 . 0.952 no
C20 H203 . 0.952 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
C18 H183 C13 124.60(9) 0.954 2.554 3.194(4) yes
loop_
_oxford_twin_element_scale_factors
0.708(4)
0.292(4)
