#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/57/1505761.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_1505761
loop_
_publ_author_name
'Sonoda, Yoriko'
'Goto, Midori'
'Tsuzuki, Seiji'
'Tamaoki, Nobuyuki'
_publ_section_title
;
 Fluorescence spectroscopic properties and crystal structure of a series
 of donor-acceptor diphenylpolyenes.
;
_journal_issue                   50
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              13379
_journal_page_last               13387
_journal_paper_doi               10.1021/jp064937j
_journal_volume                  110
_journal_year                    2006
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.950(2)
_cell_angle_beta                 82.264(2)
_cell_angle_gamma                77.374(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0445(9)
_cell_length_b                   8.5236(9)
_cell_length_c                   14.1707(15)
_cell_measurement_reflns_used    2473
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.048
_cell_measurement_theta_min      2.522
_cell_volume                     912.51(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      183(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5656
_diffrn_reflns_theta_full        26.22
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         1.49
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  811
_diffrn_standards_number         84
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.820
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                2892
_reflns_number_total             3973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp064937jsi20060801_084330.cif
_cod_data_source_block           sonoia
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               1505761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.17537(16) 2.14936(12) -0.30268(8) 0.0559(3) Uani 1 1 d .
O2 O 0.35826(16) 2.10199(13) -0.42255(8) 0.0591(4) Uani 1 1 d .
O3 O 0.27392(13) 0.06212(11) 0.26655(7) 0.0387(3) Uani 1 1 d .
N1 N 0.27837(16) 2.05498(14) -0.34415(8) 0.0374(3) Uani 1 1 d .
C1 C 0.22344(17) 1.65410(16) -0.17354(9) 0.0334(3) Uani 1 1 d .
H1 H 0.1560 1.6150 -0.1153 0.040 Uiso 1 1 calc R
C2 C 0.20446(17) 1.82203(16) -0.21405(9) 0.0344(3) Uani 1 1 d .
H2 H 0.1254 1.8984 -0.1838 0.041 Uiso 1 1 calc R
C3 C 0.30221(16) 1.87743(15) -0.29933(9) 0.0299(3) Uani 1 1 d .
C4 C 0.42030(17) 1.76960(16) -0.34452(9) 0.0334(3) Uani 1 1 d .
H4 H 0.4867 1.8097 -0.4030 0.040 Uiso 1 1 calc R
C5 C 0.43877(16) 1.60245(15) -0.30221(9) 0.0328(3) Uani 1 1 d .
H5 H 0.5206 1.5272 -0.3319 0.039 Uiso 1 1 calc R
C6 C 0.34090(16) 1.54020(15) -0.21710(9) 0.0284(3) Uani 1 1 d .
C7 C 0.36540(16) 1.36155(15) -0.17796(9) 0.0321(3) Uani 1 1 d .
H7 H 0.4566 1.2966 -0.2092 0.038 Uiso 1 1 calc R
C8 C 0.27413(16) 1.27811(15) -0.10292(9) 0.0311(3) Uani 1 1 d .
H8 H 0.1826 1.3395 -0.0698 0.037 Uiso 1 1 calc R
C9 C 0.30757(16) 1.10089(15) -0.06998(9) 0.0325(3) Uani 1 1 d .
H9 H 0.3981 1.0404 -0.1042 0.039 Uiso 1 1 calc R
C10 C 0.21984(16) 1.01456(15) 0.00588(9) 0.0320(3) Uani 1 1 d .
H10 H 0.1297 1.0753 0.0402 0.038 Uiso 1 1 calc R
C11 C 0.25230(16) 0.83740(15) 0.03879(9) 0.0315(3) Uani 1 1 d .
H11 H 0.3418 0.7759 0.0044 0.038 Uiso 1 1 calc R
C12 C 0.16394(16) 0.75315(15) 0.11522(9) 0.0310(3) Uani 1 1 d .
H12 H 0.0752 0.8173 0.1484 0.037 Uiso 1 1 calc R
C13 C 0.18921(15) 0.57432(15) 0.15278(9) 0.0278(3) Uani 1 1 d .
C14 C 0.10841(16) 0.50790(15) 0.24299(9) 0.0319(3) Uani 1 1 d .
H14 H 0.0341 0.5810 0.2776 0.038 Uiso 1 1 calc R
C15 C 0.13239(17) 0.33895(16) 0.28423(9) 0.0330(3) Uani 1 1 d .
H15 H 0.0766 0.2977 0.3464 0.040 Uiso 1 1 calc R
C16 C 0.23908(16) 0.23052(15) 0.23366(9) 0.0294(3) Uani 1 1 d .
C17 C 0.31712(17) 0.29352(15) 0.14217(9) 0.0323(3) Uani 1 1 d .
H17 H 0.3872 0.2199 0.1064 0.039 Uiso 1 1 calc R
C18 C 0.29390(16) 0.46168(15) 0.10289(9) 0.0310(3) Uani 1 1 d .
H18 H 0.3499 0.5023 0.0407 0.037 Uiso 1 1 calc R
C19 C 0.19531(18) -0.00782(16) 0.36053(9) 0.0343(3) Uani 1 1 d .
H19A H 0.0693 0.0233 0.3604 0.041 Uiso 1 1 calc R
H19B H 0.2310 0.0347 0.4118 0.041 Uiso 1 1 calc R
C20 C 0.25024(18) -0.19361(15) 0.38148(9) 0.0347(3) Uani 1 1 d .
H20A H 0.3749 -0.2240 0.3879 0.042 Uiso 1 1 calc R
H20B H 0.2265 -0.2335 0.3259 0.042 Uiso 1 1 calc R
C21 C 0.15627(17) -0.27722(15) 0.47539(9) 0.0345(3) Uani 1 1 d .
H21A H 0.1713 -0.2289 0.5294 0.041 Uiso 1 1 calc R
H21B H 0.0326 -0.2539 0.4664 0.041 Uiso 1 1 calc R
C22 C 0.21859(18) -0.46337(16) 0.50432(10) 0.0401(4) Uani 1 1 d .
H22A H 0.1988 -0.5128 0.4526 0.060 Uiso 1 1 calc R
H22B H 0.1561 -0.5100 0.5659 0.060 Uiso 1 1 calc R
H22C H 0.3411 -0.4874 0.5131 0.060 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 0.0000 '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'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 '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
C16 O3 C19 117.45(10)
O2 N1 O1 123.09(11)
O2 N1 C3 118.58(11)
O1 N1 C3 118.30(11)
C2 C1 C6 120.98(12)
C2 C1 H1 119.5
C6 C1 H1 119.5
C1 C2 C3 118.98(12)
C1 C2 H2 120.5
C3 C2 H2 120.5
C2 C3 C4 122.00(11)
C2 C3 N1 119.09(12)
C4 C3 N1 118.91(11)
C5 C4 C3 118.10(11)
C5 C4 H4 121.0
C3 C4 H4 121.0
C4 C5 C6 122.07(12)
C4 C5 H5 119.0
C6 C5 H5 119.0
C5 C6 C1 117.86(11)
C5 C6 C7 118.80(11)
C1 C6 C7 123.34(12)
C8 C7 C6 127.55(12)
C8 C7 H7 116.2
C6 C7 H7 116.2
C7 C8 C9 123.48(12)
C7 C8 H8 118.3
C9 C8 H8 118.3
C10 C9 C8 124.63(13)
C10 C9 H9 117.7
C8 C9 H9 117.7
C9 C10 C11 124.83(13)
C9 C10 H10 117.6
C11 C10 H10 117.6
C12 C11 C10 124.02(12)
C12 C11 H11 118.0
C10 C11 H11 118.0
C11 C12 C13 127.17(12)
C11 C12 H12 116.4
C13 C12 H12 116.4
C14 C13 C18 116.88(11)
C14 C13 C12 119.78(11)
C18 C13 C12 123.34(11)
C15 C14 C13 122.43(12)
C15 C14 H14 118.8
C13 C14 H14 118.8
C14 C15 C16 119.32(12)
C14 C15 H15 120.3
C16 C15 H15 120.3
O3 C16 C17 115.74(11)
O3 C16 C15 124.95(11)
C17 C16 C15 119.31(11)
C18 C17 C16 120.62(11)
C18 C17 H17 119.7
C16 C17 H17 119.7
C17 C18 C13 121.39(11)
C17 C18 H18 119.3
C13 C18 H18 119.3
O3 C19 C20 108.37(11)
O3 C19 H19A 110.0
C20 C19 H19A 110.0
O3 C19 H19B 110.0
C20 C19 H19B 110.0
H19A C19 H19B 108.4
C19 C20 C21 111.14(11)
C19 C20 H20A 109.4
C21 C20 H20A 109.4
C19 C20 H20B 109.4
C21 C20 H20B 109.4
H20A C20 H20B 108.0
C22 C21 C20 113.03(11)
C22 C21 H21A 109.0
C20 C21 H21A 109.0
C22 C21 H21B 109.0
C20 C21 H21B 109.0
H21A C21 H21B 107.8
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2256(16)
O2 N1 1.2236(15)
O3 C16 1.3667(15)
O3 C19 1.4335(15)
N1 C3 1.4619(16)
C1 C2 1.3795(18)
C1 C6 1.4034(19)
C1 H1 0.9500
C2 C3 1.3827(18)
C2 H2 0.9500
C3 C4 1.3847(19)
C4 C5 1.3781(17)
C4 H4 0.9500
C5 C6 1.3967(17)
C5 H5 0.9500
C6 C7 1.4577(16)
C7 C8 1.3420(17)
C7 H7 0.9500
C8 C9 1.4360(17)
C8 H8 0.9500
C9 C10 1.3443(19)
C9 H9 0.9500
C10 C11 1.4355(17)
C10 H10 0.9500
C11 C12 1.3438(17)
C11 H11 0.9500
C12 C13 1.4561(16)
C12 H12 0.9500
C13 C14 1.3924(17)
C13 C18 1.4034(17)
C14 C15 1.3872(17)
C14 H14 0.9500
C15 C16 1.3914(19)
C15 H15 0.9500
C16 C17 1.3893(17)
C17 C18 1.3769(17)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.5088(18)
C19 H19A 0.9900
C19 H19B 0.9900
C20 C21 1.5240(17)
C20 H20A 0.9900
C20 H20B 0.9900
C21 C22 1.5188(18)
C21 H21A 0.9900
C21 H21B 0.9900
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 0.6(2)
C1 C2 C3 C4 -0.9(2)
C1 C2 C3 N1 178.03(10)
O2 N1 C3 C2 -175.83(11)
O1 N1 C3 C2 2.08(19)
O2 N1 C3 C4 3.18(19)
O1 N1 C3 C4 -178.91(12)
C2 C3 C4 C5 0.16(19)
N1 C3 C4 C5 -178.81(10)
C3 C4 C5 C6 1.00(19)
C4 C5 C6 C1 -1.34(19)
C4 C5 C6 C7 178.71(11)
C2 C1 C6 C5 0.52(19)
C2 C1 C6 C7 -179.53(11)
C5 C6 C7 C8 -173.58(12)
C1 C6 C7 C8 6.5(2)
C6 C7 C8 C9 179.57(11)
C7 C8 C9 C10 178.92(12)
C8 C9 C10 C11 179.71(10)
C9 C10 C11 C12 179.56(12)
C10 C11 C12 C13 179.97(11)
C11 C12 C13 C14 168.26(11)
C11 C12 C13 C18 -11.1(2)
C18 C13 C14 C15 1.81(19)
C12 C13 C14 C15 -177.61(11)
C13 C14 C15 C16 -0.9(2)
C19 O3 C16 C17 -179.78(10)
C19 O3 C16 C15 -0.4(2)
C14 C15 C16 O3 179.57(11)
C14 C15 C16 C17 -1.1(2)
O3 C16 C17 C18 -178.57(11)
C15 C16 C17 C18 2.0(2)
C16 C17 C18 C13 -1.0(2)
C14 C13 C18 C17 -0.85(18)
C12 C13 C18 C17 178.55(11)
C16 O3 C19 C20 179.64(10)
O3 C19 C20 C21 -173.89(10)
C19 C20 C21 C22 -174.95(11)
