#------------------------------------------------------------------------------
#$Date: 2016-08-12 16:10:22 +0300 (Fri, 12 Aug 2016) $
#$Revision: 185772 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119125.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_7119125
loop_
_publ_author_name
'Katsuya Mutoh'
'Yoichi Kobayashi'
'Yasukazu Hirao'
'Takashi Kubo'
'Jiro Abe'
_publ_section_title
;
 Stealth fast photoswitching of negative photochromic naphthalene-bridged
 phenoxyl-imidazolyl radical complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              6797
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C35 H22 N2 O'
_chemical_formula_weight         486.54
_chemical_name_systematic
'naphthalene bridged naphthoxyl-imidazolyl radical complex'
_chemical_properties_physical    Photo-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-02-18 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.024(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.417(3)
_cell_length_b                   7.846(3)
_cell_length_c                   15.614(5)
_cell_measurement_reflns_used    3312
_cell_measurement_temperature    90.0
_cell_measurement_theta_max      26.2911
_cell_measurement_theta_min      2.7598
_cell_volume                     1206.5(7)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker SMART APEXII'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6504
_diffrn_reflns_theta_full        26.55
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_min         1.38
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_preparation       'photochromic compound'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/hexane'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_details
;
;
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0292P)²+0.2858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0728
_reflns_number_gt                4319
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc01534d2.cif
_cod_data_source_block           Ia
_cod_database_code               7119125
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6168(2) 0.2695(3) 0.47715(15) 0.0253(5) Uani d . . . 1 . .
H H1 0.5831 0.3699 0.4433 0.03 Uiso calc U . R 1 . .
C C2 0.7425(2) 0.0070(3) 0.49674(14) 0.0181(4) Uani d . . . 1 . .
C C3 0.8352(2) -0.2929(3) 0.59637(15) 0.0247(5) Uani d . . . 1 . .
H H3 0.8646 -0.3958 0.6289 0.03 Uiso calc U . R 1 . .
C C4 0.8245(2) -0.1122(3) 0.46932(14) 0.0169(4) Uani d . . . 1 . .
C C24 0.7046(2) 0.1886(3) 0.35205(14) 0.0169(4) Uani d . . . 1 . .
C C5 0.6370(2) 0.0971(3) 0.60799(15) 0.0263(5) Uani d . . . 1 . .
H H5 0.6174 0.0782 0.6625 0.032 Uiso calc U . R 1 . .
C C6 0.6894(2) 0.1541(3) 0.44529(14) 0.0188(4) Uani d . . . 1 . .
C C7 0.5916(3) 0.2415(3) 0.55912(16) 0.0302(6) Uani d . . . 1 . .
H H7 0.5426 0.3238 0.5806 0.036 Uiso calc U . R 1 . .
C C8 0.8701(2) -0.2584(3) 0.51824(15) 0.0207(5) Uani d . . . 1 . .
H H8 0.9252 -0.3363 0.4993 0.025 Uiso calc U . R 1 . .
C C9 0.7593(2) -0.1793(3) 0.62573(15) 0.0246(5) Uani d . . . 1 . .
H H9 0.7371 -0.2041 0.6788 0.03 Uiso calc U . R 1 . .
C C10 0.7131(2) -0.0251(3) 0.57829(15) 0.0220(5) Uani d . . . 1 . .
C C12 0.9781(2) -0.1725(3) 0.20622(14) 0.0174(4) Uani d . . . 1 . .
C C13 1.0394(2) -0.1757(3) 0.06933(15) 0.0242(5) Uani d . . . 1 . .
H H13 1.0376 -0.1227 0.0143 0.029 Uiso calc U . R 1 . .
C C14 1.0439(2) -0.3296(3) 0.22933(15) 0.0218(5) Uani d . . . 1 . .
H H14 1.0463 -0.3837 0.2842 0.026 Uiso calc U . R 1 . .
C C15 1.1037(2) -0.3309(3) 0.09320(15) 0.0222(5) Uani d . . . 1 . .
H H15 1.146 -0.3847 0.0549 0.027 Uiso calc U . R 1 . .
C C16 0.9775(2) -0.0966(3) 0.12510(16) 0.0242(5) Uani d . . . 1 . .
H H16 0.9341 0.0105 0.1079 0.029 Uiso calc U . R 1 . .
C C17 1.1056(2) -0.4072(3) 0.17345(16) 0.0267(5) Uani d . . . 1 . .
H H17 1.1498 -0.5138 0.1903 0.032 Uiso calc U . R 1 . .
C C18 0.6029(2) 0.1779(4) 0.02305(16) 0.0302(6) Uani d . . . 1 . .
H H18 0.5288 0.1331 -0.0249 0.036 Uiso calc U . R 1 . .
C C19 0.8203(2) 0.3083(3) 0.16204(15) 0.0220(5) Uani d . . . 1 . .
H H19 0.8959 0.3522 0.2092 0.026 Uiso calc U . R 1 . .
C C20 0.6551(2) 0.3376(4) 0.01444(17) 0.0328(6) Uani d . . . 1 . .
H H20 0.6162 0.4023 -0.0393 0.039 Uiso calc U . R 1 . .
C C21 0.6589(2) 0.0843(3) 0.10137(15) 0.0227(5) Uani d . . . 1 . .
H H21 0.6233 -0.0249 0.1072 0.027 Uiso calc U . R 1 . .
C C22 0.7672(2) 0.1495(3) 0.17163(14) 0.0187(4) Uani d . . . 1 . .
C C23 0.7632(2) 0.4026(3) 0.08373(17) 0.0288(5) Uani d . . . 1 . .
H H23 0.7985 0.5119 0.0778 0.035 Uiso calc U . R 1 . .
C C25 0.5061(2) 0.3283(3) 0.23127(14) 0.0181(4) Uani d . . . 1 . .
C C26 0.5784(2) 0.4944(3) 0.24748(15) 0.0219(5) Uani d . . . 1 . .
C C27 0.3649(2) 0.0210(3) 0.20099(15) 0.0233(5) Uani d . . . 1 . .
H H27 0.316 -0.0833 0.1915 0.028 Uiso calc U . R 1 . .
C C28 0.7161(2) 0.4965(3) 0.31182(15) 0.0230(5) Uani d . . . 1 . .
H H28 0.7659 0.6002 0.3214 0.028 Uiso calc U . R 1 . .
C C29 0.5644(2) 0.1836(3) 0.28010(14) 0.0161(4) Uani d . . . 1 . .
C C30 0.4932(2) 0.0299(3) 0.26422(14) 0.0189(4) Uani d . . . 1 . .
H H30 0.5332 -0.0692 0.2971 0.023 Uiso calc U . R 1 . .
C C31 0.7744(2) 0.3590(3) 0.35747(15) 0.0205(5) Uani d . . . 1 . .
H H31 0.866 0.3682 0.396 0.025 Uiso calc U . R 1 . .
C C32 0.3070(2) 0.1656(3) 0.15092(15) 0.0254(5) Uani d . . . 1 . .
H H32 0.2191 0.1595 0.1069 0.03 Uiso calc U . R 1 . .
C C33 0.3779(2) 0.3172(3) 0.16575(15) 0.0227(5) Uani d . . . 1 . .
H H33 0.339 0.4149 0.131 0.027 Uiso calc U . R 1 . .
C C34 0.9115(2) -0.0966(3) 0.26669(14) 0.0165(4) Uani d . . . 1 . .
C C35 0.8268(2) 0.0432(3) 0.25307(13) 0.0166(4) Uani d . . . 1 . .
C C36 0.8533(2) -0.0767(3) 0.38636(14) 0.0156(4) Uani d . . . 1 . .
N N1 0.92764(16) -0.1695(2) 0.35011(12) 0.0170(4) Uani d . . . 1 . .
N N2 0.79124(17) 0.0560(2) 0.33136(11) 0.0156(4) Uani d . . . 1 . .
O O1 0.52517(18) 0.6247(2) 0.20868(12) 0.0333(4) Uani d . . . 1 . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 C1 C7 . . 121.0(2)
C6 C1 H1 . . 119.5
C7 C1 H1 . . 119.5
C6 C2 C10 . . 119.61(19)
C6 C2 C4 . . 121.88(19)
C10 C2 C4 . . 118.51(19)
C9 C3 C8 . . 120.4(2)
C9 C3 H3 . . 119.8
C8 C3 H3 . . 119.8
C8 C4 C2 . . 120.90(19)
C8 C4 C36 . . 121.53(19)
C2 C4 C36 . . 117.53(19)
N2 C24 C31 . . 108.48(16)
N2 C24 C29 . . 109.06(16)
C31 C24 C29 . . 113.07(18)
N2 C24 C6 . . 109.95(17)
C31 C24 C6 . . 107.37(17)
C29 C24 C6 . . 108.87(16)
C7 C5 C10 . . 120.6(2)
C7 C5 H5 . . 119.7
C10 C5 H5 . . 119.7
C1 C6 C2 . . 119.5(2)
C1 C6 C24 . . 117.8(2)
C2 C6 C24 . . 122.67(19)
C5 C7 C1 . . 120.5(2)
C5 C7 H7 . . 119.8
C1 C7 H7 . . 119.8
C4 C8 C3 . . 120.1(2)
C4 C8 H8 . . 119.9
C3 C8 H8 . . 119.9
C3 C9 C10 . . 121.1(2)
C3 C9 H9 . . 119.5
C10 C9 H9 . . 119.5
C5 C10 C9 . . 122.5(2)
C5 C10 C2 . . 118.6(2)
C9 C10 C2 . . 118.8(2)
C16 C12 C14 . . 117.8(2)
C16 C12 C34 . . 123.1(2)
C14 C12 C34 . . 119.09(19)
C15 C13 C16 . . 120.6(2)
C15 C13 H13 . . 119.7
C16 C13 H13 . . 119.7
C17 C14 C12 . . 121.0(2)
C17 C14 H14 . . 119.5
C12 C14 H14 . . 119.5
C13 C15 C17 . . 119.3(2)
C13 C15 H15 . . 120.4
C17 C15 H15 . . 120.4
C13 C16 C12 . . 120.8(2)
C13 C16 H16 . . 119.6
C12 C16 H16 . . 119.6
C15 C17 C14 . . 120.6(2)
C15 C17 H17 . . 119.7
C14 C17 H17 . . 119.7
C21 C18 C20 . . 119.9(2)
C21 C18 H18 . . 120.0
C20 C18 H18 . . 120.0
C23 C19 C22 . . 120.1(2)
C23 C19 H19 . . 120.0
C22 C19 H19 . . 120.0
C23 C20 C18 . . 120.1(2)
C23 C20 H20 . . 119.9
C18 C20 H20 . . 119.9
C18 C21 C22 . . 120.2(2)
C18 C21 H21 . . 119.9
C22 C21 H21 . . 119.9
C21 C22 C19 . . 119.6(2)
C21 C22 C35 . . 118.4(2)
C19 C22 C35 . . 121.9(2)
C20 C23 C19 . . 120.1(2)
C20 C23 H23 . . 120.0
C19 C23 H23 . . 120.0
C29 C25 C33 . . 119.5(2)
C29 C25 C26 . . 121.06(18)
C33 C25 C26 . . 119.4(2)
O1 C26 C28 . . 121.1(2)
O1 C26 C25 . . 121.7(2)
C28 C26 C25 . . 117.22(19)
C30 C27 C32 . . 120.0(2)
C30 C27 H27 . . 120.0
C32 C27 H27 . . 120.0
C31 C28 C26 . . 122.4(2)
C31 C28 H28 . . 118.8
C26 C28 H28 . . 118.8
C25 C29 C30 . . 119.72(19)
C25 C29 C24 . . 121.63(19)
C30 C29 C24 . . 118.64(19)
C27 C30 C29 . . 120.4(2)
C27 C30 H30 . . 119.8
C29 C30 H30 . . 119.8
C28 C31 C24 . . 124.2(2)
C28 C31 H31 . . 117.9
C24 C31 H31 . . 117.9
C33 C32 C27 . . 119.7(2)
C33 C32 H32 . . 120.1
C27 C32 H32 . . 120.1
C32 C33 C25 . . 120.6(2)
C32 C33 H33 . . 119.7
C25 C33 H33 . . 119.7
N1 C34 C35 . . 110.46(18)
N1 C34 C12 . . 120.04(19)
C35 C34 C12 . . 129.48(19)
C34 C35 N2 . . 105.17(17)
C34 C35 C22 . . 130.51(18)
N2 C35 C22 . . 123.89(18)
N1 C36 N2 . . 111.94(18)
N1 C36 C4 . . 126.87(19)
N2 C36 C4 . . 120.91(18)
C36 N1 C34 . . 105.57(18)
C36 N2 C35 . . 106.83(17)
C36 N2 C24 . . 126.42(16)
C35 N2 C24 . . 126.75(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.373(3)
C1 C7 . 1.405(3)
C1 H1 . 0.95
C2 C6 . 1.412(3)
C2 C10 . 1.425(3)
C2 C4 . 1.424(3)
C3 C9 . 1.365(3)
C3 C8 . 1.408(3)
C3 H3 . 0.95
C4 C8 . 1.374(3)
C4 C36 . 1.449(3)
C24 N2 . 1.481(3)
C24 C31 . 1.512(3)
C24 C29 . 1.525(3)
C24 C6 . 1.539(3)
C5 C7 . 1.362(4)
C5 C10 . 1.414(3)
C5 H5 . 0.95
C7 H7 . 0.95
C8 H8 . 0.95
C9 C10 . 1.419(3)
C9 H9 . 0.95
C12 C16 . 1.398(3)
C12 C14 . 1.399(3)
C12 C34 . 1.468(3)
C13 C15 . 1.381(3)
C13 C16 . 1.388(3)
C13 H13 . 0.95
C14 C17 . 1.382(3)
C14 H14 . 0.95
C15 C17 . 1.383(3)
C15 H15 . 0.95
C16 H16 . 0.95
C17 H17 . 0.95
C18 C21 . 1.382(3)
C18 C20 . 1.390(4)
C18 H18 . 0.95
C19 C23 . 1.386(3)
C19 C22 . 1.391(3)
C19 H19 . 0.95
C20 C23 . 1.380(4)
C20 H20 . 0.95
C21 C22 . 1.390(3)
C21 H21 . 0.95
C22 C35 . 1.478(3)
C23 H23 . 0.95
C25 C29 . 1.392(3)
C25 C33 . 1.396(3)
C25 C26 . 1.485(3)
C26 O1 . 1.225(3)
C26 C28 . 1.459(3)
C27 C30 . 1.380(3)
C27 C32 . 1.398(3)
C27 H27 . 0.95
C28 C31 . 1.326(3)
C28 H28 . 0.95
C29 C30 . 1.395(3)
C30 H30 . 0.95
C31 H31 . 0.95
C32 C33 . 1.379(3)
C32 H32 . 0.95
C33 H33 . 0.95
C34 N1 . 1.381(3)
C34 C35 . 1.380(3)
C35 N2 . 1.392(2)
C36 N1 . 1.318(3)
C36 N2 . 1.370(3)
