#------------------------------------------------------------------------------
#$Date: 2016-02-04 05:38:53 +0200 (Thu, 04 Feb 2016) $
#$Revision: 175704 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/18/4031843.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_4031843
loop_
_publ_author_name
'Schmidt, Hauke C.'
'Spulber, Mariana'
'Neuburger, Markus'
'Palivan, Cornelia G.'
'Meuwly, Markus'
'Wenger, Oliver S.'
_publ_section_title
;
 Charge Transfer Pathways in Three Isomers of Naphthalene-Bridged Organic
 Mixed Valence Compounds.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              595
_journal_page_last               602
_journal_paper_doi               10.1021/acs.joc.5b02427
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C50 H42 N2 O4'
_chemical_formula_sum            'C50 H42 N2 O4'
_chemical_formula_weight         734.89
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6972(4)
_cell_length_b                   37.1771(11)
_cell_length_c                   12.9487(4)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    123
_cell_measurement_theta_max      68
_cell_measurement_theta_min      5
_cell_volume                     7556.6(4)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17915
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         68.426
_diffrn_reflns_theta_min         4.584
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3104
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.12
_refine_ls_abs_structure_details 'Flack (1983), 1599 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.03(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0237
_refine_ls_shift/su_max          0.0012164
_refine_ls_shift/su_mean         0.0001200
_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: 
 0.121 0.745E-01 0.276E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0260
_refine_ls_wR_factor_gt          0.0259
_refine_ls_wR_factor_ref         0.0259
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              44
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -15
_reflns_number_gt                3399
_reflns_number_total             3415
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0237
_oxford_refine_ls_scale          0.06129(6)
_oxford_reflns_number_all        3405
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            jo5b02427_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               4031843
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,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                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,y+1/2,z+1/2
x+1/2,y,z+1/2
x+1/2,y+1/2,z
-x,-y,z
-x,-y+1/2,z+1/2
-x+1/2,-y,z+1/2
-x+1/2,-y+1/2,z
-x+1/4,y+1/4,z+1/4
-x+1/4,y+3/4,z+3/4
-x+3/4,y+1/4,z+3/4
-x+3/4,y+3/4,z+1/4
x+1/4,-y+1/4,z+1/4
x+1/4,-y+3/4,z+3/4
x+3/4,-y+1/4,z+3/4
x+3/4,-y+3/4,z+1/4
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
_atom_site_refinement_flags_adp
N1 N 0.33903(6) 0.50726(2) 0.35334(8) 0.0226 1.0000 Uani . .
O1 O 0.12519(5) 0.61779(2) 0.21963(8) 0.0312 1.0000 Uani . .
O2 O 0.43491(6) 0.39235(2) 0.09833(8) 0.0329 1.0000 Uani . .
C1 C 0.5000 0.5000 0.82732(12) 0.0189 1.0000 Uani S T
C2 C 0.5000 0.5000 0.93812(13) 0.0231 1.0000 Uani S T
C3 C 0.44890(7) 0.52495(3) 0.99300(10) 0.0282 1.0000 Uani . .
C4 C 0.39787(8) 0.54848(3) 0.94170(10) 0.0306 1.0000 Uani . .
C5 C 0.39164(7) 0.54667(3) 0.83324(10) 0.0256 1.0000 Uani . .
C6 C 0.43886(7) 0.52260(3) 0.77615(10) 0.0200 1.0000 Uani . .
C7 C 0.41639(6) 0.51871(3) 0.66487(9) 0.0186 1.0000 Uani . .
C8 C 0.41012(7) 0.54829(3) 0.59922(10) 0.0201 1.0000 Uani . .
C9 C 0.38613(7) 0.54424(3) 0.49668(10) 0.0204 1.0000 Uani . .
C10 C 0.36502(7) 0.51040(3) 0.45771(10) 0.0194 1.0000 Uani . .
C11 C 0.36867(7) 0.48080(3) 0.52363(10) 0.0208 1.0000 Uani . .
C12 C 0.39503(6) 0.48507(3) 0.62482(9) 0.0194 1.0000 Uani . .
C13 C 0.28248(7) 0.53455(3) 0.31613(9) 0.0199 1.0000 Uani . .
C14 C 0.20739(7) 0.54119(3) 0.36947(9) 0.0201 1.0000 Uani . .
C15 C 0.15417(7) 0.56935(3) 0.34146(10) 0.0219 1.0000 Uani . .
C16 C 0.17512(7) 0.59054(3) 0.25675(10) 0.0232 1.0000 Uani . .
C17 C 0.24997(7) 0.58385(3) 0.20240(10) 0.0253 1.0000 Uani . .
C18 C 0.30327(7) 0.55613(3) 0.23190(10) 0.0232 1.0000 Uani . .
C19 C 0.04337(8) 0.62208(3) 0.26549(12) 0.0347 1.0000 Uani . .
C20 C 0.36487(7) 0.47823(3) 0.29005(10) 0.0188 1.0000 Uani . .
C21 C 0.31737(7) 0.46853(3) 0.20258(10) 0.0210 1.0000 Uani . .
C22 C 0.34315(7) 0.44005(3) 0.14092(10) 0.0236 1.0000 Uani . .
C23 C 0.41553(7) 0.42020(3) 0.16433(10) 0.0239 1.0000 Uani . .
C24 C 0.46323(7) 0.42969(3) 0.25082(10) 0.0229 1.0000 Uani . .
C25 C 0.43836(7) 0.45866(3) 0.31165(10) 0.0215 1.0000 Uani . .
C26 C 0.51348(8) 0.37425(3) 0.11525(11) 0.0359 1.0000 Uani . .
H31 H 0.4510 0.5243 1.0695 0.0361 1.0000 Uiso R .
H41 H 0.3641 0.5672 0.9794 0.0386 1.0000 Uiso R .
H51 H 0.3504 0.5616 0.7978 0.0333 1.0000 Uiso R .
H81 H 0.4260 0.5724 0.6224 0.0276 1.0000 Uiso R .
H91 H 0.3825 0.5655 0.4512 0.0248 1.0000 Uiso R .
H111 H 0.3518 0.4569 0.5002 0.0274 1.0000 Uiso R .
H121 H 0.3997 0.4643 0.6703 0.0244 1.0000 Uiso R .
H141 H 0.1929 0.5253 0.4294 0.0260 1.0000 Uiso R .
H151 H 0.1023 0.5740 0.3801 0.0286 1.0000 Uiso R .
H171 H 0.2637 0.5991 0.1432 0.0325 1.0000 Uiso R .
H181 H 0.3563 0.5518 0.1930 0.0308 1.0000 Uiso R .
H191 H 0.0486 0.6306 0.3379 0.0555 1.0000 Uiso R .
H192 H 0.0116 0.5988 0.2628 0.0548 1.0000 Uiso R .
H193 H 0.0142 0.6411 0.2244 0.0560 1.0000 Uiso R .
H211 H 0.2658 0.4824 0.1847 0.0266 1.0000 Uiso R .
H221 H 0.3114 0.4342 0.0795 0.0325 1.0000 Uiso R .
H241 H 0.5140 0.4158 0.2706 0.0278 1.0000 Uiso R .
H251 H 0.4747 0.4655 0.3697 0.0258 1.0000 Uiso R .
H261 H 0.5615 0.3915 0.1131 0.0558 1.0000 Uiso R .
H262 H 0.5200 0.3565 0.0591 0.0556 1.0000 Uiso R .
H263 H 0.5127 0.3610 0.1824 0.0551 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 0.0181 0.0091 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'
N 0.0311 0.0180 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'
O 0.0492 0.0322 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'
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
C10 . N1 C13 . 116.18(8) yes
C10 . N1 C20 . 122.21(9) yes
C13 . N1 C20 . 121.57(9) yes
C16 . O1 C19 . 116.96(9) yes
C23 . O2 C26 . 116.87(9) yes
C6 5_665 C1 C2 . 117.45(7) yes
C6 5_665 C1 C6 . 125.10(14) yes
C2 . C1 C6 . 117.45(7) yes
C1 . C2 C3 5_665 120.09(7) yes
C1 . C2 C3 . 120.09(7) yes
C3 5_665 C2 C3 . 119.82(15) yes
C2 . C3 C4 . 120.64(11) yes
C2 . C3 H31 . 117.8 no
C4 . C3 H31 . 121.6 no
C3 . C4 C5 . 119.81(11) yes
C3 . C4 H41 . 121.4 no
C5 . C4 H41 . 118.8 no
C4 . C5 C6 . 121.90(11) yes
C4 . C5 H51 . 119.4 no
C6 . C5 H51 . 118.5 no
C1 . C6 C5 . 119.46(11) yes
C1 . C6 C7 . 123.16(10) yes
C5 . C6 C7 . 117.03(10) yes
C6 . C7 C8 . 122.02(10) yes
C6 . C7 C12 . 120.21(9) yes
C8 . C7 C12 . 117.63(9) yes
C7 . C8 C9 . 121.14(10) yes
C7 . C8 H81 . 121.2 no
C9 . C8 H81 . 117.6 no
C8 . C9 C10 . 120.53(10) yes
C8 . C9 H91 . 120.0 no
C10 . C9 H91 . 119.5 no
N1 . C10 C9 . 119.19(10) yes
N1 . C10 C11 . 122.08(10) yes
C9 . C10 C11 . 118.72(10) yes
C10 . C11 C12 . 120.12(10) yes
C10 . C11 H111 . 121.2 no
C12 . C11 H111 . 118.7 no
C7 . C12 C11 . 121.80(10) yes
C7 . C12 H121 . 118.0 no
C11 . C12 H121 . 120.2 no
N1 . C13 C14 . 119.01(9) yes
N1 . C13 C18 . 121.77(10) yes
C14 . C13 C18 . 119.09(10) yes
C13 . C14 C15 . 121.01(10) yes
C13 . C14 H141 . 118.2 no
C15 . C14 H141 . 120.8 no
C14 . C15 C16 . 119.44(10) yes
C14 . C15 H151 . 120.3 no
C16 . C15 H151 . 120.2 no
C15 . C16 O1 . 124.15(10) yes
C15 . C16 C17 . 119.83(10) yes
O1 . C16 C17 . 116.00(10) yes
C16 . C17 C18 . 120.31(10) yes
C16 . C17 H171 . 118.6 no
C18 . C17 H171 . 121.1 no
C13 . C18 C17 . 120.30(10) yes
C13 . C18 H181 . 120.2 no
C17 . C18 H181 . 119.5 no
O1 . C19 H191 . 110.8 no
O1 . C19 H192 . 109.8 no
H191 . C19 H192 . 110.4 no
O1 . C19 H193 . 105.8 no
H191 . C19 H193 . 108.5 no
H192 . C19 H193 . 111.5 no
N1 . C20 C21 . 120.75(9) yes
N1 . C20 C25 . 121.33(9) yes
C21 . C20 C25 . 117.92(10) yes
C20 . C21 C22 . 120.39(10) yes
C20 . C21 H211 . 119.4 no
C22 . C21 H211 . 120.2 no
C21 . C22 C23 . 121.28(10) yes
C21 . C22 H221 . 119.9 no
C23 . C22 H221 . 118.8 no
C22 . C23 O2 . 116.44(10) yes
C22 . C23 C24 . 118.74(10) yes
O2 . C23 C24 . 124.81(10) yes
C23 . C24 C25 . 120.06(10) yes
C23 . C24 H241 . 120.9 no
C25 . C24 H241 . 119.1 no
C20 . C25 C24 . 121.58(10) yes
C20 . C25 H251 . 120.1 no
C24 . C25 H251 . 118.3 no
O2 . C26 H261 . 110.5 no
O2 . C26 H262 . 107.0 no
H261 . C26 H262 . 109.5 no
O2 . C26 H263 . 110.9 no
H261 . C26 H263 . 110.7 no
H262 . C26 H263 . 108.2 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 C10 . 1.4165(14) yes
N1 C13 . 1.4317(14) yes
N1 C20 . 1.4143(14) yes
O1 C16 . 1.3679(13) yes
O1 C19 . 1.4240(16) yes
O2 C23 . 1.3767(13) yes
O2 C26 . 1.4218(16) yes
C1 C6 5_665 1.4373(13) yes
C1 C2 . 1.435(2) yes
C1 C6 . 1.4373(13) yes
C2 C3 5_665 1.4172(14) yes
C2 C3 . 1.4172(14) yes
C3 C4 . 1.3593(18) yes
C3 H31 . 0.991 no
C4 C5 . 1.4095(16) yes
C4 H41 . 1.002 no
C5 C6 . 1.3772(16) yes
C5 H51 . 0.969 no
C6 C7 . 1.4905(15) yes
C7 C8 . 1.3933(15) yes
C7 C12 . 1.3951(15) yes
C8 C9 . 1.3883(15) yes
C8 H81 . 0.978 no
C9 C10 . 1.3956(15) yes
C9 H91 . 0.986 no
C10 C11 . 1.3938(15) yes
C11 C12 . 1.3831(15) yes
C11 H111 . 0.974 no
C12 H121 . 0.975 no
C13 C14 . 1.3883(15) yes
C13 C18 . 1.3927(16) yes
C14 C15 . 1.3877(15) yes
C14 H141 . 1.001 no
C15 C16 . 1.3901(16) yes
C15 H151 . 0.972 no
C16 C17 . 1.3919(17) yes
C17 C18 . 1.3814(16) yes
C17 H171 . 0.979 no
C18 H181 . 0.985 no
C19 H191 . 0.993 no
C19 H192 . 1.000 no
C19 H193 . 0.996 no
C20 C21 . 1.4032(15) yes
C20 C25 . 1.3922(15) yes
C21 C22 . 1.3865(15) yes
C21 H211 . 0.987 no
C22 C23 . 1.3883(16) yes
C22 H221 . 0.964 no
C23 C24 . 1.3926(16) yes
C24 C25 . 1.3905(15) yes
C24 H241 . 0.983 no
C25 H251 . 0.977 no
C26 H261 . 0.989 no
C26 H262 . 0.987 no
C26 H263 . 1.000 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 H91 O1 13_565 137.86(3) 0.986 2.495 3.2938(16) yes
