#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/13/7111380.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_7111380
loop_
_publ_author_name
'Mei, Xuefeng'
'Wolf, Christian'
_publ_section_title
;
 A highly congested N,N?-dioxide fluorosensor for enantioselective
 recognition of chiral hydrogen bond donorsElectronic supplementary
 information (ESI) available: experimental procedures and analytical data
 for 1 including Stern?Volmer and Benesi?Hildebrand plots. See
 http://www.rsc.org/suppdata/cc/b4/b407718k/
;
_journal_issue                   18
_journal_name_full               'Chemical Communications'
_journal_page_first              2078
_journal_page_last               2079
_journal_paper_doi               10.1039/b407718k
_journal_year                    2004
_chemical_formula_moiety         'C28 H23 N2 O1.5'
_chemical_formula_sum            'C28 H23 N2 O1.5'
_chemical_formula_weight         411.48
_chemical_name_common
;1,8-Bis(3,3'-bis(3,5-dimethylphenyl)-9,9'-diacridyl)
naphthalene-N,N-dioxide
;
_chemical_name_systematic
;
1,8-Bis(3,3'-bis(3,5-dimethylphenyl)-9,9'-diacridyl)
naphthalene-N,N-dioxide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.204(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.551(2)
_cell_length_b                   13.3883(12)
_cell_length_c                   13.7187(12)
_cell_measurement_reflns_used    6145
_cell_measurement_temperature    186(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.16
_cell_volume                     4307.5(6)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      186(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18167
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_correction_T_min  0.9289
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0776P)²+3.1342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                3491
_reflns_number_total             4690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b407718ksup1.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'Monoclininc' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        4307.5(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C28 H23 N2 O1.50'
_cod_database_code               7111380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.44954(6) 0.16420(9) 0.09252(10) 0.0287(3) Uani 1 1 d .
O1S O 0.5000 0.30691(17) 0.2500 0.0457(6) Uani 1 2 d S
N1 N 0.46424(6) 0.07004(11) 0.10616(11) 0.0223(3) Uani 1 1 d .
N1S N 0.2704(2) -0.2337(3) 0.2601(4) 0.152(2) Uani 1 1 d .
C1 C 0.39233(8) -0.17373(13) 0.09308(14) 0.0237(4) Uani 1 1 d .
H1 H 0.4008 -0.2429 0.1029 0.028 Uiso 1 1 calc R
C2 C 0.33685(8) -0.14385(15) 0.06238(15) 0.0271(4) Uani 1 1 d .
H2 H 0.3075 -0.1927 0.0498 0.032 Uiso 1 1 calc R
C3 C 0.32187(8) -0.04078(14) 0.04868(14) 0.0256(4) Uani 1 1 d .
C4 C 0.36456(8) 0.02843(14) 0.06341(14) 0.0245(4) Uani 1 1 d .
H4 H 0.3553 0.0973 0.0540 0.029 Uiso 1 1 calc R
C5 C 0.56252(8) 0.11900(14) 0.14317(14) 0.0275(4) Uani 1 1 d .
H5 H 0.5514 0.1870 0.1320 0.033 Uiso 1 1 calc R
C6 C 0.61884(8) 0.09356(15) 0.17006(15) 0.0303(4) Uani 1 1 d .
H6 H 0.6469 0.1444 0.1783 0.036 Uiso 1 1 calc R
C7 C 0.63597(8) -0.00700(15) 0.18572(15) 0.0286(4) Uani 1 1 d .
H7 H 0.6753 -0.0234 0.2034 0.034 Uiso 1 1 calc R
C8 C 0.59668(8) -0.08087(14) 0.17581(13) 0.0246(4) Uani 1 1 d .
H8 H 0.6090 -0.1483 0.1867 0.030 Uiso 1 1 calc R
C9 C 0.49569(7) -0.13254(13) 0.14331(13) 0.0205(4) Uani 1 1 d .
C10 C 0.43791(7) -0.10375(13) 0.11083(13) 0.0210(4) Uani 1 1 d .
C11 C 0.42239(7) -0.00165(13) 0.09256(13) 0.0215(4) Uani 1 1 d .
C12 C 0.52081(7) 0.04361(13) 0.13209(13) 0.0216(4) Uani 1 1 d .
C13 C 0.53704(7) -0.05877(13) 0.14929(13) 0.0206(4) Uani 1 1 d .
C14 C 0.50985(7) -0.24070(13) 0.16421(13) 0.0205(4) Uani 1 1 d .
C15 C 0.52524(8) -0.29483(14) 0.09134(14) 0.0249(4) Uani 1 1 d .
H15 H 0.5333 -0.2610 0.0363 0.030 Uiso 1 1 calc R
C16 C 0.52926(8) -0.39981(14) 0.09712(15) 0.0284(4) Uani 1 1 d .
H16 H 0.5417 -0.4356 0.0479 0.034 Uiso 1 1 calc R
C17 C 0.51543(8) -0.45038(14) 0.17256(15) 0.0266(4) Uani 1 1 d .
H17 H 0.5161 -0.5213 0.1734 0.032 Uiso 1 1 calc R
C18 C 0.5000 -0.39741(19) 0.2500 0.0223(5) Uani 1 2 d S
C19 C 0.5000 -0.29095(18) 0.2500 0.0196(5) Uani 1 2 d S
C20 C 0.26083(8) -0.01126(15) 0.02077(15) 0.0288(4) Uani 1 1 d .
C21 C 0.24059(9) 0.07317(16) -0.03809(16) 0.0333(5) Uani 1 1 d .
H21 H 0.2665 0.1140 -0.0597 0.040 Uiso 1 1 calc R
C22 C 0.18290(9) 0.09879(17) -0.06591(17) 0.0383(5) Uani 1 1 d .
C23 C 0.14591(9) 0.03786(17) -0.03314(17) 0.0384(5) Uani 1 1 d .
H23 H 0.1065 0.0539 -0.0530 0.046 Uiso 1 1 calc R
C24 C 0.16464(8) -0.04564(16) 0.02761(16) 0.0345(5) Uani 1 1 d .
C25 C 0.22232(8) -0.06945(16) 0.05368(16) 0.0315(5) Uani 1 1 d .
H25 H 0.2359 -0.1266 0.0948 0.038 Uiso 1 1 calc R
C26 C 0.12489(9) -0.10766(18) 0.06759(19) 0.0429(6) Uani 1 1 d .
H26A H 0.1419 -0.1736 0.0878 0.064 Uiso 1 1 calc R
H26B H 0.0885 -0.1155 0.0141 0.064 Uiso 1 1 calc R
H26C H 0.1184 -0.0744 0.1268 0.064 Uiso 1 1 calc R
C27 C 0.16129(11) 0.1898(2) -0.1312(2) 0.0564(7) Uani 1 1 d .
H27A H 0.1933 0.2232 -0.1468 0.085 Uiso 0.50 1 calc PR
H27B H 0.1435 0.2359 -0.0942 0.085 Uiso 0.50 1 calc PR
H27C H 0.1331 0.1693 -0.1949 0.085 Uiso 0.50 1 calc PR
H27D H 0.1200 0.1957 -0.1438 0.085 Uiso 0.50 1 calc PR
H27E H 0.1697 0.1830 -0.1964 0.085 Uiso 0.50 1 calc PR
H27F H 0.1801 0.2497 -0.0957 0.085 Uiso 0.50 1 calc PR
C1S C 0.32050(16) -0.3952(3) 0.2436(3) 0.0828(11) Uani 1 1 d .
H1S1 H 0.3127 -0.4124 0.1713 0.124 Uiso 1 1 calc R
H1S2 H 0.3073 -0.4493 0.2790 0.124 Uiso 1 1 calc R
H1S3 H 0.3616 -0.3857 0.2743 0.124 Uiso 1 1 calc R
C2S C 0.29164(13) -0.3063(3) 0.2524(3) 0.0696(9) Uani 1 1 d .
H1S H 0.4825(13) 0.261(2) 0.203(2) 0.078(10) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 N1 C12 119.98(15) . .
O1 N1 C11 119.24(14) . .
C12 N1 C11 120.78(15) . .
C2 C1 C10 121.55(17) . .
C1 C2 C3 121.36(17) . .
C4 C3 C2 118.65(17) . .
C4 C3 C20 121.85(17) . .
C2 C3 C20 119.49(17) . .
C3 C4 C11 120.63(17) . .
C6 C5 C12 119.65(18) . .
C5 C6 C7 120.86(18) . .
C8 C7 C6 120.61(18) . .
C7 C8 C13 121.13(18) . .
C13 C9 C10 118.02(16) . .
C13 C9 C14 123.20(16) . .
C10 C9 C14 118.70(15) . .
C9 C10 C11 120.74(16) . .
C9 C10 C1 122.73(16) . .
C11 C10 C1 116.52(16) . .
N1 C11 C4 119.06(16) . .
N1 C11 C10 119.73(16) . .
C4 C11 C10 121.19(16) . .
N1 C12 C5 119.24(16) . .
N1 C12 C13 120.09(15) . .
C5 C12 C13 120.66(16) . .
C9 C13 C12 120.35(16) . .
C9 C13 C8 122.55(16) . .
C12 C13 C8 117.07(16) . .
C15 C14 C19 119.85(17) . .
C15 C14 C9 117.95(16) . .
C19 C14 C9 121.61(16) . .
C14 C15 C16 120.94(17) . .
C17 C16 C15 120.65(17) . .
C16 C17 C18 120.17(18) . .
C17 C18 C17 120.0(2) 2_655 .
C17 C18 C19 119.99(12) 2_655 .
C17 C18 C19 119.99(12) . .
C18 C19 C14 117.92(11) . 2_655
C18 C19 C14 117.92(11) . .
C14 C19 C14 124.2(2) 2_655 .
C21 C20 C25 118.68(18) . .
C21 C20 C3 121.66(18) . .
C25 C20 C3 119.66(18) . .
C20 C21 C22 121.1(2) . .
C23 C22 C21 118.3(2) . .
C23 C22 C27 121.1(2) . .
C21 C22 C27 120.6(2) . .
C24 C23 C22 122.29(19) . .
C23 C24 C25 118.0(2) . .
C23 C24 C26 121.88(19) . .
C25 C24 C26 120.1(2) . .
C24 C25 C20 121.5(2) . .
N1S C2S C1S 177.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.3094(19) .
N1 C12 1.374(2) .
N1 C11 1.378(2) .
N1S C2S 1.123(5) .
C1 C2 1.361(3) .
C1 C10 1.424(3) .
C2 C3 1.426(3) .
C3 C4 1.368(3) .
C3 C20 1.486(3) .
C4 C11 1.415(3) .
C5 C6 1.365(3) .
C5 C12 1.414(3) .
C6 C7 1.408(3) .
C7 C8 1.360(3) .
C8 C13 1.431(2) .
C9 C13 1.401(2) .
C9 C10 1.409(2) .
C9 C14 1.497(2) .
C10 C11 1.421(2) .
C12 C13 1.427(2) .
C14 C15 1.375(2) .
C14 C19 1.437(2) .
C15 C16 1.410(3) .
C16 C17 1.361(3) .
C17 C18 1.419(2) .
C18 C17 1.419(2) 2_655
C18 C19 1.425(3) .
C19 C14 1.437(2) 2_655
C20 C21 1.393(3) .
C20 C25 1.399(3) .
C21 C22 1.396(3) .
C22 C23 1.390(3) .
C22 C27 1.512(3) .
C23 C24 1.389(3) .
C24 C25 1.391(3) .
C24 C26 1.503(3) .
C1S C2S 1.408(5) .
