#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/47/1504723.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_1504723
loop_
_publ_author_name
'Memminger, Karin'
'Oeser, Thomas'
'Müller, Thomas J J'
_publ_section_title
;
 Phenothiazinophanes: synthesis, structure, and intramolecular electronic
 communication.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2797
_journal_page_last               2800
_journal_paper_doi               10.1021/ol800920d
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C48 H46 N2 S2'
_chemical_formula_weight         714.99
_chemical_name_systematic
;
 1(10),4(10)-Di-n-hexyl-1,4(3,7)-diphenothiazinacyclophan-2,5-di-(1,2-phenylene)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 90.176(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.7557(4)
_cell_length_b                   15.0846(3)
_cell_length_c                   7.9914(1)
_cell_measurement_temperature    200(2)
_cell_volume                     1899.29(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17880
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.29
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamina
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0430
_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)+(0.0663P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                2556
_reflns_number_total             3865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800920d-file004.cif
_cod_data_source_block           km1
_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_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504723
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.42658(4) 0.34047(4) -0.00080(7) 0.02747(18) Uani 1 1 d .
C1 C 0.35429(13) 0.42907(14) 0.0277(3) 0.0236(5) Uani 1 1 d .
C2 C 0.32973(13) 0.48202(14) -0.1050(3) 0.0249(5) Uani 1 1 d .
H2 H 0.3544 0.4728 -0.2119 0.030 Uiso 1 1 calc R
C3 C 0.27000(13) 0.54800(14) -0.0847(3) 0.0251(5) Uani 1 1 d .
C4 C 0.23740(14) 0.56246(14) 0.0734(3) 0.0279(5) Uani 1 1 d .
H4 H 0.1968 0.6082 0.0896 0.033 Uiso 1 1 calc R
C5 C 0.26302(14) 0.51139(15) 0.2085(3) 0.0279(5) Uani 1 1 d .
H5 H 0.2408 0.5235 0.3165 0.033 Uiso 1 1 calc R
C6 C 0.32091(13) 0.44249(14) 0.1880(3) 0.0238(5) Uani 1 1 d .
N1 N 0.34795(11) 0.38657(12) 0.3204(2) 0.0259(4) Uani 1 1 d .
C8 C 0.43701(14) 0.37530(14) 0.3338(3) 0.0237(5) Uani 1 1 d .
C9 C 0.48205(14) 0.38446(15) 0.4831(3) 0.0291(5) Uani 1 1 d .
H9 H 0.4525 0.3968 0.5838 0.035 Uiso 1 1 calc R
C10 C 0.56974(14) 0.37568(15) 0.4860(3) 0.0284(5) Uani 1 1 d .
H10 H 0.5990 0.3814 0.5895 0.034 Uiso 1 1 calc R
C11 C 0.61566(14) 0.35873(14) 0.3418(3) 0.0252(5) Uani 1 1 d .
C12 C 0.57064(14) 0.34766(14) 0.1925(3) 0.0252(5) Uani 1 1 d .
H12 H 0.6005 0.3346 0.0924 0.030 Uiso 1 1 calc R
C13 C 0.48326(14) 0.35542(14) 0.1882(3) 0.0245(5) Uani 1 1 d .
C14 C 0.71052(14) 0.35652(14) 0.3493(3) 0.0268(5) Uani 1 1 d .
C15 C 0.74965(15) 0.31159(15) 0.4819(3) 0.0329(6) Uani 1 1 d .
H15 H 0.7152 0.2817 0.5614 0.040 Uiso 1 1 calc R
C16 C 0.83663(16) 0.30932(16) 0.5009(3) 0.0375(6) Uani 1 1 d .
H16 H 0.8614 0.2789 0.5931 0.045 Uiso 1 1 calc R
C17 C 0.88747(15) 0.35134(16) 0.3857(3) 0.0376(6) Uani 1 1 d .
H17 H 0.9475 0.3502 0.3978 0.045 Uiso 1 1 calc R
C18 C 0.85063(15) 0.39497(16) 0.2530(3) 0.0343(6) Uani 1 1 d .
H18 H 0.8862 0.4233 0.1736 0.041 Uiso 1 1 calc R
C19 C 0.76266(14) 0.39915(14) 0.2309(3) 0.0270(5) Uani 1 1 d .
C20 C 0.29763(14) 0.38737(16) 0.4758(3) 0.0319(6) Uani 1 1 d .
H20A H 0.2950 0.4487 0.5195 0.038 Uiso 1 1 calc R
H20B H 0.3263 0.3502 0.5609 0.038 Uiso 1 1 calc R
C21 C 0.20776(14) 0.35301(17) 0.4486(3) 0.0352(6) Uani 1 1 d .
H21A H 0.1720 0.3730 0.5430 0.042 Uiso 1 1 calc R
H21B H 0.1846 0.3801 0.3452 0.042 Uiso 1 1 calc R
C22 C 0.20052(15) 0.25286(17) 0.4341(3) 0.0365(6) Uani 1 1 d .
H22A H 0.2185 0.2253 0.5409 0.044 Uiso 1 1 calc R
H22B H 0.2392 0.2317 0.3452 0.044 Uiso 1 1 calc R
C23 C 0.11037(14) 0.22401(17) 0.3933(3) 0.0379(6) Uani 1 1 d .
H23A H 0.0713 0.2532 0.4730 0.046 Uiso 1 1 calc R
H23B H 0.0958 0.2455 0.2798 0.046 Uiso 1 1 calc R
C24 C 0.09495(16) 0.12531(17) 0.3995(4) 0.0460(7) Uani 1 1 d .
H24A H 0.1011 0.1046 0.5165 0.055 Uiso 1 1 calc R
H24B H 0.1386 0.0949 0.3316 0.055 Uiso 1 1 calc R
C25 C 0.00783(17) 0.0997(2) 0.3351(4) 0.0614(9) Uani 1 1 d .
H25A H -0.0356 0.1325 0.3972 0.092 Uiso 1 1 calc R
H25B H -0.0008 0.0359 0.3506 0.092 Uiso 1 1 calc R
H25C H 0.0035 0.1143 0.2159 0.092 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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_3
C13 S1 C1 96.74(10) .
C2 C1 C6 120.9(2) .
C2 C1 S1 121.08(17) .
C6 C1 S1 118.02(16) .
C3 C2 C1 121.1(2) .
C2 C3 C4 118.5(2) .
C2 C3 C19 121.6(2) 3_665
C4 C3 C19 119.9(2) 3_665
C3 C4 C5 121.1(2) .
C4 C5 C6 120.8(2) .
C5 C6 C1 117.6(2) .
C5 C6 N1 123.5(2) .
C1 C6 N1 118.92(19) .
C8 N1 C6 115.05(17) .
C8 N1 C20 118.12(17) .
C6 N1 C20 117.53(17) .
C9 C8 C13 117.7(2) .
C9 C8 N1 123.7(2) .
C13 C8 N1 118.55(18) .
C10 C9 C8 120.6(2) .
C11 C10 C9 121.7(2) .
C10 C11 C12 117.9(2) .
C10 C11 C14 119.66(19) .
C12 C11 C14 122.4(2) .
C13 C12 C11 120.9(2) .
C12 C13 C8 121.07(19) .
C12 C13 S1 120.73(17) .
C8 C13 S1 118.19(16) .
C15 C14 C19 118.2(2) .
C15 C14 C11 118.6(2) .
C19 C14 C11 123.17(19) .
C16 C15 C14 122.1(2) .
C17 C16 C15 119.7(2) .
C18 C17 C16 119.4(2) .
C17 C18 C19 122.4(2) .
C18 C19 C14 118.3(2) .
C18 C19 C3 117.3(2) 3_665
C14 C19 C3 124.35(19) 3_665
N1 C20 C21 112.25(18) .
C22 C21 C20 114.8(2) .
C21 C22 C23 111.8(2) .
C24 C23 C22 115.2(2) .
C23 C24 C25 112.7(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C13 1.767(2) .
S1 C1 1.771(2) .
C1 C2 1.382(3) .
C1 C6 1.401(3) .
C2 C3 1.380(3) .
C3 C4 1.382(3) .
C3 C19 1.503(3) 3_665
C4 C5 1.386(3) .
C5 C6 1.393(3) .
C6 N1 1.417(3) .
N1 C8 1.417(3) .
N1 C20 1.476(3) .
C8 C9 1.393(3) .
C8 C13 1.407(3) .
C9 C10 1.388(3) .
C10 C11 1.386(3) .
C11 C12 1.396(3) .
C11 C14 1.496(3) .
C12 C13 1.382(3) .
C14 C15 1.400(3) .
C14 C19 1.410(3) .
C15 C16 1.379(3) .
C16 C17 1.377(3) .
C17 C18 1.375(3) .
C18 C19 1.398(3) .
C19 C3 1.504(3) 3_665
C20 C21 1.523(3) .
C21 C22 1.519(3) .
C22 C23 1.520(3) .
C23 C24 1.509(3) .
C24 C25 1.514(3) .
