#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150965.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_7150965
loop_
_publ_author_name
'Matsuhira, Takashi'
'Tsuchihashi, Kazuki'
'Yamamoto, Hitoshi'
'Okamura, Taka-aki'
'Ueyama, Norikazu'
_publ_section_title
;
 Novel photosystem involving protonation and deprotonation processes
 modelled on a PYP photocycle
;
_journal_issue                   17
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3118
_journal_page_last               3126
_journal_paper_doi               10.1039/b807417h
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         ' C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.28
_chemical_name_systematic
;
?
;
_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                90.00
_cell_angle_beta                 103.58(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.000(6)
_cell_length_b                   12.348(6)
_cell_length_c                   9.398(7)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1240.8(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11384
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0697
_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)+(0.0367P)²+0.4805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                1705
_reflns_number_total             2835
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b807417h.txt
_cod_data_source_block           shelxl_2
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        ' C13 H17 N O2'
_cod_database_code               7150965
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O01 O 0.55974(14) 0.43812(12) 0.17240(18) 0.0413(4) Uani 1 1 d . . .
H01 H 0.507(2) 0.3819(19) 0.144(3) 0.050 Uiso 1 1 d . . .
O02 O 0.43006(14) 0.27946(11) 0.05640(17) 0.0416(4) Uani 1 1 d . . .
N1 N 0.37465(17) 0.10782(14) 0.0982(2) 0.0366(5) Uani 1 1 d . . .
H1 H 0.396(2) 0.0493(18) 0.153(3) 0.044 Uiso 1 1 d . . .
C1 C 0.6739(2) 0.40946(17) 0.1509(2) 0.0350(5) Uani 1 1 d . . .
C2 C 0.7391(2) 0.48731(18) 0.0923(3) 0.0414(6) Uani 1 1 d . . .
H2 H 0.7010 0.5552 0.0624 0.050 Uiso 1 1 calc R . .
C3 C 0.8579(2) 0.4669(2) 0.0774(3) 0.0489(6) Uani 1 1 d . . .
H3 H 0.9018 0.5207 0.0374 0.059 Uiso 1 1 calc R . .
C4 C 0.9143(2) 0.3680(2) 0.1202(3) 0.0492(6) Uani 1 1 d . . .
H4 H 0.9962 0.3532 0.1087 0.059 Uiso 1 1 calc R . .
C5 C 0.8499(2) 0.29157(18) 0.1798(3) 0.0407(6) Uani 1 1 d . . .
H5 H 0.8898 0.2247 0.2118 0.049 Uiso 1 1 calc R . .
C6 C 0.72794(19) 0.30855(16) 0.1949(2) 0.0337(5) Uani 1 1 d . . .
C7 C 0.6727(2) 0.22474(17) 0.2733(3) 0.0388(5) Uani 1 1 d . . .
H7 H 0.7296 0.1990 0.3589 0.047 Uiso 1 1 calc R . .
C8 C 0.5607(2) 0.17742(17) 0.2505(3) 0.0381(5) Uani 1 1 d . . .
H8 H 0.5505 0.1266 0.3227 0.046 Uiso 1 1 calc R . .
C9 C 0.4507(2) 0.19342(17) 0.1280(2) 0.0345(5) Uani 1 1 d . . .
C10 C 0.2603(2) 0.10082(18) -0.0204(2) 0.0385(5) Uani 1 1 d . . .
C11 C 0.1652(2) 0.1835(2) 0.0044(3) 0.0533(7) Uani 1 1 d . . .
H11A H 0.1458 0.1703 0.0995 0.064 Uiso 1 1 calc R . .
H11B H 0.0886 0.1770 -0.0734 0.064 Uiso 1 1 calc R . .
H11C H 0.1998 0.2565 0.0029 0.064 Uiso 1 1 calc R . .
C12 C 0.2077(2) -0.01303(19) -0.0148(3) 0.0558(7) Uani 1 1 d . . .
H12A H 0.2691 -0.0664 -0.0308 0.067 Uiso 1 1 calc R . .
H12B H 0.1305 -0.0206 -0.0914 0.067 Uiso 1 1 calc R . .
H12C H 0.1897 -0.0252 0.0812 0.067 Uiso 1 1 calc R . .
C13 C 0.2931(2) 0.1181(2) -0.1674(3) 0.0538(7) Uani 1 1 d . . .
H13A H 0.3545 0.0637 -0.1803 0.065 Uiso 1 1 calc R . .
H13B H 0.3286 0.1907 -0.1702 0.065 Uiso 1 1 calc R . .
H13C H 0.2175 0.1111 -0.2463 0.065 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'
O O 0.0106 0.0060 '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
C1 O01 H01 108.1(14) . . ?
C9 N1 C10 125.86(19) . . ?
C9 N1 H1 117.0(15) . . ?
C10 N1 H1 117.1(15) . . ?
O01 C1 C2 117.26(19) . . ?
O01 C1 C6 121.87(19) . . ?
C2 C1 C6 120.7(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.00(19) . . ?
C5 C6 C7 117.50(19) . . ?
C1 C6 C7 125.00(19) . . ?
C8 C7 C6 134.2(2) . . ?
C8 C7 H7 112.9 . . ?
C6 C7 H7 112.9 . . ?
C7 C8 C9 128.6(2) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
O02 C9 N1 122.3(2) . . ?
O02 C9 C8 123.1(2) . . ?
N1 C9 C8 114.60(19) . . ?
N1 C10 C11 109.93(19) . . ?
N1 C10 C13 109.60(19) . . ?
C11 C10 C13 111.3(2) . . ?
N1 C10 C12 106.94(18) . . ?
C11 C10 C12 109.5(2) . . ?
C13 C10 C12 109.5(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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
O01 C1 1.365(3) . ?
O01 H01 0.91(2) . ?
O02 C9 1.250(2) . ?
N1 C9 1.336(3) . ?
N1 C10 1.474(3) . ?
N1 H1 0.88(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.481(3) . ?
C7 C8 1.334(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.474(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.518(3) . ?
C10 C13 1.523(3) . ?
C10 C12 1.526(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O01 C1 C2 C3 175.4(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C4 C5 C6 C7 -174.3(2) . . . . ?
O01 C1 C6 C5 -174.3(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
O01 C1 C6 C7 -2.6(3) . . . . ?
C2 C1 C6 C7 172.9(2) . . . . ?
C5 C6 C7 C8 -137.4(3) . . . . ?
C1 C6 C7 C8 51.1(4) . . . . ?
C6 C7 C8 C9 2.1(4) . . . . ?
C10 N1 C9 O02 1.0(3) . . . . ?
C10 N1 C9 C8 -178.33(19) . . . . ?
C7 C8 C9 O02 -27.0(4) . . . . ?
C7 C8 C9 N1 152.3(2) . . . . ?
C9 N1 C10 C11 -63.2(3) . . . . ?
C9 N1 C10 C13 59.5(3) . . . . ?
C9 N1 C10 C12 178.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653429
