#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150437.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_7150437
loop_
_publ_author_name
'Petersen, Michael Axman'
'Nielsen, Iben B.'
'Kristensen, Michael B.'
'Kadziola, Anders'
'Lammich, Lutz'
'Andersen, Lars H.'
'Nielsen, Mogens Brøndsted'
_publ_section_title
;
 Novel retinylidene iminium salts for defining opsin shifts: synthesis
 and intrinsic chromophoric properties.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1546
_journal_page_last               1554
_journal_paper_doi               10.1039/b600121a
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_sum            'C22 H29 N'
_chemical_formula_weight         307.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus/SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.8840(16)
_cell_length_b                   11.7110(11)
_cell_length_c                   16.091(2)
_cell_measurement_reflns_used    27434
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      32.98
_cell_measurement_theta_min      2.15
_cell_volume                     1862.6(4)
_computing_cell_refinement       'COLLECT (Nonius, 1999)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg, 2003)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      122(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            50833
_diffrn_reflns_theta_full        32.98
_diffrn_reflns_theta_max         32.98
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         6990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0431
_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)+(0.0535P)²+0.2845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                6132
_reflns_number_total             6990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b600121a.txt
_cod_data_source_block           shelxl2
_cod_database_code               7150437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.68506(13) 0.20313(11) -0.53260(8) 0.0406(3) Uani 1 1 d . . .
C2 C 0.13433(11) -0.30182(9) -0.50686(7) 0.0262(2) Uani 1 1 d . . .
H2A H 0.2253 -0.2674 -0.5010 0.031 Uiso 1 1 calc R . .
H2B H 0.1462 -0.3817 -0.5257 0.031 Uiso 1 1 calc R . .
C3 C 0.05507(12) -0.23594(10) -0.57239(7) 0.0275(2) Uani 1 1 d . . .
H3A H -0.0361 -0.2699 -0.5789 0.033 Uiso 1 1 calc R . .
H3B H 0.1023 -0.2406 -0.6265 0.033 Uiso 1 1 calc R . .
C4 C 0.06394(10) -0.30184(8) -0.42179(6) 0.01989(17) Uani 1 1 d . . .
C5 C 0.16955(12) -0.33819(10) -0.35642(8) 0.0310(2) Uani 1 1 d . . .
H5A H 0.1236 -0.3572 -0.3043 0.037 Uiso 1 1 calc R . .
H5B H 0.2331 -0.2753 -0.3469 0.037 Uiso 1 1 calc R . .
H5C H 0.2191 -0.4052 -0.3766 0.037 Uiso 1 1 calc R . .
C6 C -0.05104(12) -0.39045(9) -0.42142(8) 0.0269(2) Uani 1 1 d . . .
H6A H -0.0151 -0.4652 -0.4376 0.032 Uiso 1 1 calc R . .
H6B H -0.1213 -0.3672 -0.4609 0.032 Uiso 1 1 calc R . .
H6C H -0.0899 -0.3954 -0.3655 0.032 Uiso 1 1 calc R . .
C7 C 0.04236(11) -0.11164(9) -0.54589(7) 0.0248(2) Uani 1 1 d . . .
H7A H 0.1305 -0.0732 -0.5542 0.030 Uiso 1 1 calc R . .
H7B H -0.0248 -0.0733 -0.5820 0.030 Uiso 1 1 calc R . .
C8 C 0.00577(9) -0.18356(8) -0.40095(6) 0.01793(16) Uani 1 1 d . . .
C9 C -0.00009(10) -0.09741(8) -0.45639(6) 0.01964(17) Uani 1 1 d . . .
C10 C -0.04653(13) 0.02211(9) -0.43632(8) 0.0273(2) Uani 1 1 d . . .
H10A H 0.0184 0.0773 -0.4589 0.033 Uiso 1 1 calc R . .
H10B H -0.0524 0.0314 -0.3759 0.033 Uiso 1 1 calc R . .
H10C H -0.1357 0.0354 -0.4612 0.033 Uiso 1 1 calc R . .
C11 C -0.04652(10) -0.17253(8) -0.31521(6) 0.02025(17) Uani 1 1 d . . .
H11 H 0.0129 -0.1913 -0.2709 0.024 Uiso 1 1 calc R . .
C12 C -0.17236(10) -0.13775(9) -0.29554(6) 0.01968(17) Uani 1 1 d . . .
H12 H -0.2294 -0.1121 -0.3392 0.024 Uiso 1 1 calc R . .
C13 C -0.22646(11) -0.13703(9) -0.21113(6) 0.02163(19) Uani 1 1 d . . .
C14 C -0.13657(13) -0.18161(11) -0.14300(7) 0.0298(2) Uani 1 1 d . . .
H14A H -0.1865 -0.1819 -0.0904 0.036 Uiso 1 1 calc R . .
H14B H -0.0568 -0.1324 -0.1378 0.036 Uiso 1 1 calc R . .
H14C H -0.1079 -0.2596 -0.1564 0.036 Uiso 1 1 calc R . .
C15 C -0.35418(12) -0.10286(9) -0.19230(6) 0.0242(2) Uani 1 1 d . . .
H15 H -0.3795 -0.1119 -0.1357 0.029 Uiso 1 1 calc R . .
C16 C -0.45843(11) -0.05429(9) -0.24610(6) 0.02263(19) Uani 1 1 d . . .
C17 C -0.43361(11) 0.02360(9) -0.30687(7) 0.02330(19) Uani 1 1 d . . .
H17 H -0.3446 0.0534 -0.3122 0.028 Uiso 1 1 calc R . .
C18 C -0.60131(12) -0.09362(11) -0.22845(7) 0.0290(2) Uani 1 1 d . . .
H18A H -0.6140 -0.1003 -0.1676 0.035 Uiso 1 1 calc R . .
H18B H -0.6149 -0.1703 -0.2530 0.035 Uiso 1 1 calc R . .
C19 C -0.53705(11) 0.06324(9) -0.36404(7) 0.0242(2) Uani 1 1 d . . .
C20 C -0.70703(12) -0.01217(12) -0.26335(9) 0.0333(3) Uani 1 1 d . . .
H20A H -0.7064 0.0598 -0.2310 0.040 Uiso 1 1 calc R . .
H20B H -0.7980 -0.0469 -0.2583 0.040 Uiso 1 1 calc R . .
C21 C -0.67727(11) 0.01359(11) -0.35461(8) 0.0293(2) Uani 1 1 d . . .
H21A H -0.6843 -0.0576 -0.3876 0.035 Uiso 1 1 calc R . .
H21B H -0.7449 0.0684 -0.3762 0.035 Uiso 1 1 calc R . .
C22 C -0.50646(12) 0.13919(10) -0.42489(7) 0.0276(2) Uani 1 1 d . . .
H22 H -0.4173 0.1692 -0.4282 0.033 Uiso 1 1 calc R . .
C23 C -0.60553(13) 0.17513(11) -0.48428(8) 0.0317(2) Uani 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'
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
_geom_angle_publ_flag
C3 C2 C4 112.58(8) . . ?
C3 C2 H2A 109.1 . . ?
C4 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C4 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C7 109.45(10) . . ?
C2 C3 H3A 109.8 . . ?
C7 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C7 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C6 C4 C2 109.76(9) . . ?
C6 C4 C8 109.31(8) . . ?
C2 C4 C8 111.34(8) . . ?
C6 C4 C5 108.13(9) . . ?
C2 C4 C5 107.54(9) . . ?
C8 C4 C5 110.69(9) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C7 C3 113.32(9) . . ?
C9 C7 H7A 108.9 . . ?
C3 C7 H7A 108.9 . . ?
C9 C7 H7B 108.9 . . ?
C3 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C11 122.48(9) . . ?
C9 C8 C4 123.12(9) . . ?
C11 C8 C4 114.39(8) . . ?
C8 C9 C10 124.48(9) . . ?
C8 C9 C7 122.47(9) . . ?
C10 C9 C7 113.05(9) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 124.65(9) . . ?
C12 C11 H11 117.7 . . ?
C8 C11 H11 117.7 . . ?
C11 C12 C13 123.98(9) . . ?
C11 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C15 C13 C12 123.34(10) . . ?
C15 C13 C14 119.24(10) . . ?
C12 C13 C14 117.37(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 129.64(9) . . ?
C13 C15 H15 115.2 . . ?
C16 C15 H15 115.2 . . ?
C17 C16 C15 124.06(10) . . ?
C17 C16 C18 120.53(10) . . ?
C15 C16 C18 115.38(9) . . ?
C16 C17 C19 122.91(10) . . ?
C16 C17 H17 118.5 . . ?
C19 C17 H17 118.5 . . ?
C16 C18 C20 112.39(10) . . ?
C16 C18 H18A 109.1 . . ?
C20 C18 H18A 109.1 . . ?
C16 C18 H18B 109.1 . . ?
C20 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C22 C19 C17 120.66(10) . . ?
C22 C19 C21 121.95(11) . . ?
C17 C19 C21 117.35(10) . . ?
C18 C20 C21 110.25(10) . . ?
C18 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
C18 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C19 C21 C20 110.44(10) . . ?
C19 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C19 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C19 C22 C23 121.47(11) . . ?
C19 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
N1 C23 C22 179.31(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C23 1.1532(18) . ?
C2 C3 1.5234(16) . ?
C2 C4 1.5356(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.5220(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.5390(14) . ?
C4 C8 1.5368(13) . ?
C4 C5 1.5418(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C9 1.5092(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3480(13) . ?
C8 C11 1.4789(14) . ?
C9 C10 1.5080(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3465(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.4598(14) . ?
C12 H12 0.9500 . ?
C13 C15 1.3585(16) . ?
C13 C14 1.5046(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.4610(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3596(15) . ?
C16 C18 1.5124(16) . ?
C17 C19 1.4516(16) . ?
C17 H17 0.9500 . ?
C18 C20 1.5222(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C22 1.3570(16) . ?
C19 C21 1.5106(16) . ?
C20 C21 1.5278(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.4315(18) . ?
C22 H22 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C2 C3 C7 61.55(12) . . . . ?
C3 C2 C4 C6 79.02(11) . . . . ?
C3 C2 C4 C8 -42.15(12) . . . . ?
C3 C2 C4 C5 -163.57(10) . . . . ?
C2 C3 C7 C9 -46.75(13) . . . . ?
C6 C4 C8 C9 -111.90(11) . . . . ?
C2 C4 C8 C9 9.54(13) . . . . ?
C5 C4 C8 C9 129.10(10) . . . . ?
C6 C4 C8 C11 66.74(11) . . . . ?
C2 C4 C8 C11 -171.82(8) . . . . ?
C5 C4 C8 C11 -52.25(11) . . . . ?
C11 C8 C9 C10 6.36(15) . . . . ?
C4 C8 C9 C10 -175.11(9) . . . . ?
C11 C8 C9 C7 -174.69(9) . . . . ?
C4 C8 C9 C7 3.84(15) . . . . ?
C3 C7 C9 C8 15.51(15) . . . . ?
C3 C7 C9 C10 -165.43(10) . . . . ?
C9 C8 C11 C12 53.19(15) . . . . ?
C4 C8 C11 C12 -125.46(11) . . . . ?
C8 C11 C12 C13 174.28(9) . . . . ?
C11 C12 C13 C15 -179.26(10) . . . . ?
C11 C12 C13 C14 -2.03(15) . . . . ?
C12 C13 C15 C16 -4.60(17) . . . . ?
C14 C13 C15 C16 178.22(10) . . . . ?
C13 C15 C16 C17 -40.14(17) . . . . ?
C13 C15 C16 C18 141.76(11) . . . . ?
C15 C16 C17 C19 174.63(10) . . . . ?
C18 C16 C17 C19 -7.36(15) . . . . ?
C17 C16 C18 C20 -18.49(14) . . . . ?
C15 C16 C18 C20 159.68(9) . . . . ?
C16 C17 C19 C22 -178.48(10) . . . . ?
C16 C17 C19 C21 -0.52(15) . . . . ?
C16 C18 C20 C21 50.45(13) . . . . ?
C22 C19 C21 C20 -148.95(11) . . . . ?
C17 C19 C21 C20 33.12(14) . . . . ?
C18 C20 C21 C19 -57.49(13) . . . . ?
C17 C19 C22 C23 176.99(10) . . . . ?
C21 C19 C22 C23 -0.88(17) . . . . ?
C19 C22 C23 N1 -85(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653352
