#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:49:31 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178918 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/47/4114770.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_4114770
loop_
_publ_author_name
'Glenn P. Bartholomew'
'Guillermo C. Bazan'
_publ_section_title
;
 Synthesis, Characterization, and Spectroscopy of
 4,7,12,15-[2.2]Paracyclophane Containing Donor and Acceptor Groups:
 Impact of Substitution Patterns on Through-Space Charge Transfer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5183
_journal_page_last               5196
_journal_paper_doi               10.1021/ja0121383
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C96 H140 N4'
_chemical_formula_weight         1350.12
_chemical_name_systematic
4,7,12,15-tetra(4'-dihexylaminostyryl)[2.2]paracyclophane
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 131.1180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.858(3)
_cell_length_b                   16.2284(13)
_cell_length_c                   21.780(2)
_cell_measurement_temperature    293(2)
_cell_volume                     8483.1(13)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_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  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28312
_diffrn_reflns_theta_max         22.00
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.060
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_F_000             2976
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   2.343
_refine_ls_goodness_of_fit_obs   3.033
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         5163
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      2.474
_refine_ls_restrained_S_obs      3.060
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_obs          0.1037
_refine_ls_shift/esd_max         -0.423
_refine_ls_shift/esd_mean        0.028
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2678
_refine_ls_wR_factor_obs         0.2375
_reflns_number_observed          2898
_reflns_number_total             5204
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja0121383_3.cif
_cod_data_source_block           datam
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        8483.1(12)
_cod_database_code               4114770
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N -0.0349(2) 0.7565(2) 0.0168(3) 0.0837(14) Uani 1 d .
N2 N 0.1859(3) -0.2844(4) 0.5170(4) 0.118(2) Uani 1 d .
C11 C -0.0208(2) 0.6835(3) 0.0584(3) 0.0667(14) Uani 1 d .
C12 C 0.0064(2) 0.6814(3) 0.1414(4) 0.070(2) Uani 1 d .
H12 H 0.0171(17) 0.7327(26) 0.1718(25) 0.075(15) Uiso 1 d .
C13 C 0.0210(2) 0.6071(3) 0.1825(4) 0.0706(15) Uani 1 d .
H13 H 0.0387(15) 0.6103(21) 0.2417(25) 0.058(13) Uiso 1 d .
C14 C 0.0091(2) 0.5319(3) 0.1452(3) 0.0611(13) Uani 1 d .
C15 C -0.0183(3) 0.5353(4) 0.0626(4) 0.083(2) Uani 1 d .
H15 H -0.0212(16) 0.4877(25) 0.0397(24) 0.061(14) Uiso 1 d .
C16 C -0.0318(3) 0.6080(3) 0.0216(4) 0.080(2) Uani 1 d .
H16 H -0.0511(18) 0.6093(25) -0.0339(29) 0.075(17) Uiso 1 d .
C17 C 0.0255(2) 0.4551(3) 0.1920(3) 0.0656(14) Uani 1 d .
H17 H 0.0444(22) 0.4669(29) 0.2603(35) 0.132(20) Uiso 1 d .
C18 C 0.0127(2) 0.3786(3) 0.1621(4) 0.0651(14) Uani 1 d .
H18 H -0.0113(17) 0.3630(25) 0.1045(27) 0.075(16) Uiso 1 d .
C21 C 0.0310(2) 0.3020(3) 0.2092(3) 0.0610(13) Uani 1 d .
C22 C 0.0663(2) 0.3030(3) 0.2941(4) 0.0647(15) Uani 1 d .
H22 H 0.0746(19) 0.3518(28) 0.3170(29) 0.085(18) Uiso 1 d .
C23 C 0.0810(2) 0.2334(3) 0.3410(3) 0.0606(13) Uani 1 d .
C24 C 0.0712(2) 0.1566(3) 0.3041(3) 0.0593(13) Uani 1 d .
C25 C 0.0351(2) 0.1548(3) 0.2192(3) 0.0613(14) Uani 1 d .
H25 H 0.0235(15) 0.1040(24) 0.1908(22) 0.054(13) Uiso 1 d .
C26 C 0.0102(2) 0.2249(3) 0.1715(3) 0.0596(13) Uani 1 d .
C27 C 0.0951(2) 0.2421(3) 0.4215(3) 0.0734(15) Uani 1 d .
H27A H 0.1048(2) 0.2990(3) 0.4396(3) 0.088 Uiso 1 calc R
H27B H 0.1271(2) 0.2080(3) 0.4619(3) 0.088 Uiso 1 calc R
C28 C -0.0443(2) 0.2158(3) 0.0861(3) 0.0701(15) Uani 1 d .
H28A H -0.0490(2) 0.1588(3) 0.0691(3) 0.084 Uiso 1 calc R
H28B H -0.0438(2) 0.2495(3) 0.0498(3) 0.084 Uiso 1 calc R
C31 C 0.1600(2) -0.2158(3) 0.4726(4) 0.075(2) Uani 1 d .
C32 C 0.1778(3) -0.1390(4) 0.5063(4) 0.100(2) Uani 1 d .
H32 H 0.2095(26) -0.1275(33) 0.5613(38) 0.129(24) Uiso 1 d .
C33 C 0.1515(3) -0.0686(4) 0.4602(4) 0.097(2) Uani 1 d .
H33 H 0.1666(17) -0.0163(28) 0.4906(26) 0.078(15) Uiso 1 d .
C34 C 0.1065(2) -0.0705(3) 0.3781(3) 0.0618(13) Uani 1 d .
C35 C 0.0881(2) -0.1476(3) 0.3443(4) 0.074(2) Uani 1 d .
H35 H 0.0539(19) -0.1537(23) 0.2825(28) 0.074(14) Uiso 1 d .
C36 C 0.1140(3) -0.2190(4) 0.3906(4) 0.082(2) Uani 1 d .
H36 H 0.1021(22) -0.2628(29) 0.3654(31) 0.092(21) Uiso 1 d .
C37 C 0.0802(2) 0.0031(3) 0.3278(4) 0.0650(14) Uani 1 d .
H37 H 0.0509(17) -0.0048(22) 0.2667(27) 0.062(14) Uiso 1 d .
C38 C 0.0929(2) 0.0802(3) 0.3526(4) 0.0656(14) Uani 1 d .
H38 H 0.1227(16) 0.0899(21) 0.4119(26) 0.053(13) Uiso 1 d .
C41 C -0.0638(3) 0.7560(3) -0.0709(4) 0.091(2) Uani 1 d D
H41A H -0.0492(3) 0.7114(3) -0.0818(4) 0.110 Uiso 1 calc R
H41B H -0.0563(3) 0.8074(3) -0.0849(4) 0.110 Uiso 1 calc R
C42 C -0.1250(3) 0.7456(4) -0.1226(5) 0.124(2) Uani 1 d D
H42A H -0.1402(3) 0.7938(4) -0.1169(5) 0.149 Uiso 1 calc R
H42B H -0.1322(3) 0.6982(4) -0.1035(5) 0.149 Uiso 1 calc R
C43 C -0.1540(4) 0.7337(6) -0.2109(5) 0.174(4) Uani 1 d D
H43A H -0.1841(4) 0.7734(6) -0.2429(5) 0.208 Uiso 1 calc R
H43B H -0.1278(4) 0.7454(6) -0.2185(5) 0.208 Uiso 1 calc R
C44 C -0.1751(8) 0.6574(9) -0.2399(9) 0.343(11) Uani 1 d D
H44A H -0.2044(8) 0.6542(9) -0.2374(9) 0.412 Uiso 1 calc R
H44B H -0.1457(8) 0.6218(9) -0.1963(9) 0.412 Uiso 1 calc R
C45 C -0.1998(6) 0.6068(16) -0.3187(8) 0.515(21) Uani 1 d D
H45A H -0.1835(6) 0.6218(16) -0.3423(8) 0.618 Uiso 1 calc R
H45B H -0.1977(6) 0.5477(16) -0.3105(8) 0.618 Uiso 1 calc R
C46 C -0.2544(8) 0.6389(9) -0.3629(10) 0.414(14) Uani 1 d D
H46A H -0.2775(30) 0.5978(57) -0.3663(134) 0.622 Uiso 1 calc R
H46B H -0.2698(41) 0.6538(146) -0.4169(53) 0.622 Uiso 1 calc R
H46C H -0.2528(16) 0.6868(95) -0.3355(85) 0.622 Uiso 1 calc R
C51 C -0.0269(3) 0.8360(3) 0.0523(4) 0.092(2) Uani 1 d .
H51A H -0.0268(3) 0.8307(3) 0.0968(4) 0.110 Uiso 1 calc R
H51B H -0.0572(3) 0.8725(3) 0.0117(4) 0.110 Uiso 1 calc R
C52 C 0.0302(3) 0.8729(5) 0.0848(5) 0.151(3) Uani 1 d .
H52A H 0.0594(3) 0.8350(5) 0.1251(5) 0.181 Uiso 1 calc R
H52B H 0.0296(3) 0.8738(5) 0.0397(5) 0.181 Uiso 1 calc R
C53 C 0.0446(5) 0.9488(6) 0.1182(6) 0.198(4) Uani 1 d .
H53A H 0.0406(5) 0.9495(6) 0.1587(6) 0.238 Uiso 1 calc R
H53B H 0.0174(5) 0.9872(6) 0.0757(6) 0.238 Uiso 1 calc R
C54 C 0.1005(6) 0.9818(8) 0.1574(10) 0.259(7) Uani 1 d D
H54A H 0.0970(6) 1.0403(8) 0.1622(10) 0.311 Uiso 1 calc R
H54B H 0.1238(6) 0.9605(8) 0.2126(10) 0.311 Uiso 1 calc R
C55 C 0.1325(7) 0.9787(10) 0.1404(12) 0.370(13) Uani 1 d D
H55A H 0.1132(7) 1.0027(10) 0.0870(12) 0.444 Uiso 1 calc R
H55B H 0.1404(7) 0.9216(10) 0.1383(12) 0.444 Uiso 1 calc R
C56 C 0.1895(5) 1.0263(6) 0.2055(8) 0.271(7) Uani 1 d D
H56A H 0.2131(21) 1.0185(62) 0.1931(43) 0.407 Uiso 1 calc R
H56B H 0.2077(25) 1.0051(53) 0.2590(11) 0.407 Uiso 1 calc R
H56C H 0.1822(6) 1.0840(13) 0.2038(54) 0.407 Uiso 1 calc R
C61 C 0.1567(4) -0.3799(7) 0.4879(5) 0.194(5) Uani 1 d D
H61A H 0.1695(4) -0.4136(7) 0.5342(5) 0.233 Uiso 1 calc R
H61B H 0.1163(4) -0.3773(7) 0.4495(5) 0.233 Uiso 1 calc R
C62 C 0.1763(6) -0.4074(10) 0.4523(9) 0.280(8) Uani 1 d D
H62A H 0.2165(6) -0.4038(10) 0.4874(9) 0.335 Uiso 1 calc R
H62B H 0.1583(6) -0.3822(10) 0.3998(9) 0.335 Uiso 1 calc R
C63 C 0.1534(6) -0.5026(8) 0.4456(9) 0.264(6) Uani 1 d D
H63A H 0.1250(6) -0.5005(8) 0.4498(9) 0.317 Uiso 1 calc R
H63B H 0.1371(6) -0.5265(8) 0.3932(9) 0.317 Uiso 1 calc R
C64 C 0.2019(7) -0.5552(7) 0.5138(12) 0.312(10) Uani 1 d D
H64A H 0.2087(7) -0.5357(7) 0.5618(12) 0.375 Uiso 1 calc R
H64B H 0.1856(7) -0.6095(7) 0.5029(12) 0.375 Uiso 1 calc R
C65 C 0.2562(9) -0.5721(13) 0.5432(17) 0.536(26) Uani 1 d D
H65A H 0.2574(9) -0.5748(13) 0.4998(17) 0.643 Uiso 1 calc R
H65B H 0.2839(9) -0.5333(13) 0.5847(17) 0.643 Uiso 1 calc R
C66 C 0.2608(8) -0.6499(9) 0.5753(13) 0.361(11) Uani 1 d D
H66A H 0.2867(64) -0.6470(30) 0.6337(14) 0.541 Uiso 1 calc R
H66B H 0.2738(79) -0.6892(26) 0.5581(99) 0.541 Uiso 1 calc R
H66C H 0.2250(19) -0.6667(56) 0.5560(100) 0.541 Uiso 1 calc R
C71 C 0.2340(5) -0.2787(5) 0.6157(8) 0.214(6) Uani 1 d .
H71A H 0.2283(5) -0.2323(5) 0.6376(8) 0.257 Uiso 1 calc R
H71B H 0.2367(5) -0.3291(5) 0.6422(8) 0.257 Uiso 1 calc R
C72 C 0.2759(5) -0.2685(5) 0.6211(6) 0.172(4) Uani 1 d .
H72A H 0.2707(5) -0.2224(5) 0.5883(6) 0.206 Uiso 1 calc R
H72B H 0.2844(5) -0.3177(5) 0.6058(6) 0.206 Uiso 1 calc R
C73 C 0.3281(4) -0.2475(6) 0.7276(6) 0.156(3) Uani 1 d .
H73A H 0.3258(4) -0.2894(6) 0.7570(6) 0.187 Uiso 1 calc R
H73B H 0.3644(4) -0.2527(6) 0.7431(6) 0.187 Uiso 1 calc R
C74 C 0.3251(5) -0.1684(9) 0.7535(10) 0.244(6) Uani 1 d .
H74A H 0.2868(5) -0.1565(9) 0.7280(10) 0.292 Uiso 1 calc R
H74B H 0.3377(5) -0.1262(9) 0.7373(10) 0.292 Uiso 1 calc R
C75 C 0.3609(6) -0.1685(13) 0.8438(9) 0.297(10) Uani 1 d .
H75A H 0.3462(6) -0.2058(13) 0.8605(9) 0.357 Uiso 1 calc R
H75B H 0.3987(6) -0.1848(13) 0.8701(9) 0.357 Uiso 1 calc R
C76 C 0.3594(6) -0.0828(12) 0.8646(11) 0.360(13) Uani 1 d .
H76A H 0.3848(63) -0.0767(31) 0.9228(11) 0.541 Uiso 1 calc R
H76B H 0.3224(20) -0.0695(42) 0.8423(107) 0.541 Uiso 1 calc R
H76C H 0.3701(81) -0.0463(14) 0.8423(102) 0.541 Uiso 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'
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
C11 N1 C51 123.6(5) .
C11 N1 C41 120.2(4) .
C51 N1 C41 116.1(4) .
C31 N2 C71 120.2(6) .
C31 N2 C61 124.0(6) .
C71 N2 C61 110.7(6) .
N1 C11 C16 122.4(5) .
N1 C11 C12 121.9(5) .
C16 C11 C12 115.8(5) .
C13 C12 C11 120.9(5) .
C14 C13 C12 123.1(6) .
C13 C14 C15 115.1(5) .
C13 C14 C17 120.5(5) .
C15 C14 C17 124.4(5) .
C16 C15 C14 122.6(6) .
C15 C16 C11 122.5(6) .
C18 C17 C14 126.4(5) .
C17 C18 C21 126.4(5) .
C22 C21 C26 116.4(5) .
C22 C21 C18 121.3(5) .
C26 C21 C18 122.0(5) .
C23 C22 C21 123.7(5) .
C22 C23 C24 117.6(5) .
C22 C23 C27 118.7(4) .
C24 C23 C27 122.4(4) .
C25 C24 C23 117.2(5) .
C25 C24 C38 121.5(5) .
C23 C24 C38 120.9(5) .
C26 C25 C24 122.9(5) .
C25 C26 C21 118.5(5) .
C25 C26 C28 118.3(4) .
C21 C26 C28 122.0(4) .
C23 C27 C28 110.7(4) 2
C26 C28 C27 112.1(4) 2
N2 C31 C32 121.9(6) .
N2 C31 C36 121.9(6) .
C32 C31 C36 116.2(6) .
C31 C32 C33 121.7(7) .
C34 C33 C32 122.9(6) .
C33 C34 C35 115.6(5) .
C33 C34 C37 123.6(5) .
C35 C34 C37 120.8(5) .
C34 C35 C36 121.9(6) .
C31 C36 C35 121.7(6) .
C38 C37 C34 126.9(6) .
C37 C38 C24 129.2(6) .
N1 C41 C42 111.7(5) .
C41 C42 C43 112.4(6) .
C44 C43 C42 114.4(9) .
C43 C44 C45 136.6(13) .
C46 C45 C44 93.4(16) .
N1 C51 C52 109.1(5) .
C53 C52 C51 118.3(8) .
C52 C53 C54 119.8(11) .
C55 C54 C53 134.2(16) .
C54 C55 C56 112.3(16) .
C62 C61 N2 99.6(12) .
C61 C62 C63 90.9(10) .
C64 C63 C62 109.2(10) .
C65 C64 C63 134.6(18) .
C66 C65 C64 95.4(16) .
C72 C71 N2 98.5(9) .
C71 C72 C73 99.7(9) .
C74 C73 C72 115.8(9) .
C73 C74 C75 109.2(14) .
C76 C75 C74 104.7(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.375(5) .
N1 C51 1.437(6) .
N1 C41 1.479(6) .
N2 C31 1.344(6) .
N2 C71 1.627(12) .
N2 C61 1.702(12) .
C11 C16 1.377(6) .
C11 C12 1.400(6) .
C12 C13 1.386(6) .
C13 C14 1.374(6) .
C14 C15 1.392(7) .
C14 C17 1.472(6) .
C15 C16 1.367(7) .
C17 C18 1.336(6) .
C18 C21 1.466(6) .
C21 C22 1.397(6) .
C21 C26 1.401(6) .
C22 C23 1.383(6) .
C23 C24 1.402(6) .
C23 C27 1.504(6) .
C24 C25 1.396(6) .
C24 C38 1.473(6) .
C25 C26 1.385(6) .
C26 C28 1.500(6) .
C27 C28 1.573(6) 2
C28 C27 1.573(6) 2
C31 C32 1.367(7) .
C31 C36 1.378(7) .
C32 C33 1.380(7) .
C33 C34 1.372(7) .
C34 C35 1.372(6) .
C34 C37 1.457(6) .
C35 C36 1.394(7) .
C37 C38 1.318(6) .
C41 C42 1.487(7) .
C42 C43 1.502(8) .
C43 C44 1.352(11) .
C44 C45 1.57(2) .
C45 C46 1.42(2) .
C51 C52 1.573(9) .
C52 C53 1.349(9) .
C53 C54 1.478(13) .
C54 C55 1.30(2) .
C55 C56 1.586(14) .
C61 C62 1.351(11) .
C62 C63 1.673(13) .
C63 C64 1.518(13) .
C64 C65 1.422(15) .
C65 C66 1.40(2) .
C71 C72 1.273(10) .
C72 C73 1.786(12) .
C73 C74 1.431(12) .
C74 C75 1.489(14) .
C75 C76 1.47(2) .
