#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/19/2201997.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201997
loop_
_publ_author_name
'Wang, Ruihu'
'Xu, Lijin'
'Chen, Gang'
'Zhou, Zhongyuan'
'Hong, Maochun'
'Cao, Rong'
'Chan, Albert S. C.'
_publ_section_title
;
 (S)-2,2'-Bis(4-nitro-2-pyridyloxy)-1,1'-binaphthalene
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o865
_journal_page_last               o867
_journal_paper_doi               10.1107/S1600536803009292
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C30 H18 N4 O6'
_chemical_formula_moiety         'C30 H18 N4 O6'
_chemical_formula_sum            'C30 H18 N4 O6'
_chemical_formula_weight         530.48
_chemical_name_systematic
;
(S)-2,2'-Bis(4-nitro-2-pyridyloxy)-1,1'-binaphthalene
;
_space_group_IT_number           1
_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                96.859(3)
_cell_angle_beta                 104.061(4)
_cell_angle_gamma                108.599(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4573(14)
_cell_length_b                   7.9472(15)
_cell_length_c                   11.748(2)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.97
_cell_volume                     625.3(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SMART
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'ω scan'
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4222
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  .990
_exptl_absorpt_correction_T_min  .980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             274
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .10
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.153
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0549P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2651
_reflns_number_total             3405
_reflns_threshold_expression     'I >2σ(I)'
_cod_data_source_file            fl6032.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2201997
_cod_database_fobs_code          2201997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N11 0.8994(3) 1.4718(3) 0.6792(2) 0.0508(6) Uani d . 1 . . N
N12 0.6068(5) 1.1724(5) 0.3822(3) 0.0904(11) Uani d . 1 . . N
N41 0.7372(3) 2.0857(3) 0.9541(2) 0.0474(5) Uani d . 1 . . N
N42 1.0922(5) 2.3974(4) 1.2341(3) 0.0731(8) Uani d . 1 . . N
O1 1.0205(3) 1.7844(2) 0.73700(16) 0.0497(5) Uani d . 1 . . O
O2 0.7769(3) 2.0176(2) 0.76743(16) 0.0488(5) Uani d . 1 . . O
O11 0.5237(6) 1.1860(5) 0.2832(3) 0.1308(14) Uani d . 1 . . O
O12 0.6097(6) 1.0278(4) 0.4060(3) 0.1287(13) Uani d . 1 . . O
O41 0.9873(5) 2.3671(5) 1.2999(2) 0.1033(9) Uani d . 1 . . O
O42 1.2626(4) 2.5062(4) 1.2671(3) 0.1033(10) Uani d . 1 . . O
C11 0.9116(4) 1.6301(3) 0.6509(2) 0.0424(6) Uani d . 1 . . C
C12 0.8244(5) 1.6532(4) 0.5391(3) 0.0534(7) Uani d . 1 . . C
H12 0.828(5) 1.771(5) 0.532(3) 0.072(10) Uiso d . 1 . . H
C13 0.7217(5) 1.5043(5) 0.4508(3) 0.0659(9) Uani d . 1 . . C
H13 0.661(6) 1.500(5) 0.371(4) 0.090(12) Uiso d . 1 . . H
C14 0.7100(5) 1.3369(4) 0.4771(3) 0.0583(8) Uani d . 1 . . C
C15 0.7973(5) 1.3243(4) 0.5909(3) 0.0578(8) Uani d . 1 . . C
H15 0.791(5) 1.205(5) 0.606(3) 0.078(10) Uiso d . 1 . . H
C21 0.8549(4) 1.7445(3) 0.8889(2) 0.0382(5) Uani d . 1 . . C
C22 1.0261(4) 1.7775(3) 0.8561(2) 0.0421(6) Uani d . 1 . . C
C23 1.2132(4) 1.8250(4) 0.9397(3) 0.0506(7) Uani d . 1 . . C
H23 1.325(5) 1.842(3) 0.909(3) 0.050(8) Uiso d . 1 . . H
C24 1.2296(5) 1.8401(4) 1.0582(3) 0.0561(7) Uani d . 1 . . C
H24 1.360(5) 1.884(4) 1.116(3) 0.069(10) Uiso d . 1 . . H
C25 1.0741(6) 1.8291(5) 1.2218(3) 0.0698(9) Uani d . 1 . . C
H25 1.211(6) 1.869(5) 1.282(4) 0.085(11) Uiso d . 1 . . H
C26 0.9127(6) 1.8030(5) 1.2592(3) 0.0775(11) Uani d . 1 . . C
H26 0.914(5) 1.813(5) 1.338(4) 0.078(11) Uiso d . 1 . . H
C27 0.7244(6) 1.7488(5) 1.1766(3) 0.0702(10) Uani d . 1 . . C
H27 0.619(6) 1.731(5) 1.200(4) 0.082(12) Uiso d . 1 . . H
C28 0.7024(5) 1.7237(4) 1.0560(3) 0.0519(7) Uani d . 1 . . C
H28 0.569(5) 1.684(4) 0.996(3) 0.061(9) Uiso d . 1 . . H
C29 0.8705(4) 1.7559(3) 1.0132(2) 0.0409(6) Uani d . 1 . . C
C30 1.0604(4) 1.8066(4) 1.0991(2) 0.0506(7) Uani d . 1 . . C
C31 0.6645(4) 1.7068(3) 0.7939(2) 0.0376(5) Uani d . 1 . . C
C32 0.6342(4) 1.8412(3) 0.7370(2) 0.0400(6) Uani d . 1 . . C
C33 0.4739(4) 1.8067(4) 0.6340(2) 0.0457(6) Uani d . 1 . . C
H33 0.456(4) 1.901(4) 0.597(3) 0.049(7) Uiso d . 1 . . H
C34 0.3444(4) 1.6336(4) 0.5859(3) 0.0490(6) Uani d . 1 . . C
H34 0.245(4) 1.613(4) 0.517(3) 0.048(7) Uiso d . 1 . . H
C35 0.2345(4) 1.3073(4) 0.5902(3) 0.0531(7) Uani d . 1 . . C
H35 0.138(4) 1.286(4) 0.518(3) 0.049(8) Uiso d . 1 . . H
C36 0.2542(5) 1.1708(4) 0.6439(3) 0.0593(8) Uani d . 1 . . C
H36 0.167(5) 1.057(5) 0.611(3) 0.066(9) Uiso d . 1 . . H
C37 0.4052(4) 1.2072(4) 0.7517(3) 0.0536(7) Uani d . 1 . . C
H37 0.414(4) 1.116(4) 0.784(3) 0.048(8) Uiso d . 1 . . H
C38 0.5363(4) 1.3783(3) 0.8012(3) 0.0440(6) Uani d . 1 . . C
H38 0.643(4) 1.406(3) 0.881(3) 0.045(7) Uiso d . 1 . . H
C39 0.5218(4) 1.5258(3) 0.7474(2) 0.0383(5) Uani d . 1 . . C
C40 0.3639(4) 1.4893(3) 0.6404(2) 0.0420(6) Uani d . 1 . . C
C41 0.8507(4) 2.1131(3) 0.8834(2) 0.0426(6) Uani d . 1 . . C
C42 1.0413(5) 2.2406(4) 0.9151(3) 0.0615(8) Uani d . 1 . . C
H42 1.119(5) 2.250(5) 0.859(3) 0.084(11) Uiso d . 1 . . H
C43 1.1225(5) 2.3363(5) 1.0316(3) 0.0662(9) Uani d . 1 . . C
H43 1.257(6) 2.419(5) 1.063(3) 0.074(10) Uiso d . 1 . . H
C44 1.0086(5) 2.3035(4) 1.1081(3) 0.0536(7) Uani d . 1 . . C
C45 0.8172(5) 2.1804(4) 1.0673(3) 0.0512(7) Uani d . 1 . . C
H45 0.733(4) 2.153(4) 1.120(3) 0.057(8) Uiso d . 1 . . H
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
_geom_angle_publ_flag
C11 N11 C15 116.6(3) ?
O11 N12 O12 123.0(4) yes
O11 N12 C14 118.6(4) ?
O12 N12 C14 118.4(4) ?
C41 N41 C45 117.0(2) ?
O41 N42 O42 123.6(3) yes
O41 N42 C44 118.5(3) ?
O42 N42 C44 117.9(3) ?
C11 O1 C22 118.1(2) yes
C41 O2 C32 120.5(2) yes
N11 C11 O1 118.5(2) ?
N11 C11 C12 125.1(2) ?
O1 C11 C12 116.4(2) ?
C13 C12 C11 118.0(3) ?
C13 C12 H12 124(2) ?
C11 C12 H12 117(2) ?
C12 C13 C14 118.2(3) ?
C12 C13 H13 127(2) ?
C14 C13 H13 114(2) ?
C15 C14 C13 120.5(3) ?
C15 C14 N12 119.8(3) ?
C13 C14 N12 119.7(3) ?
N11 C15 C14 121.7(3) ?
N11 C15 H15 119(2) ?
C14 C15 H15 119(2) ?
C22 C21 C29 117.9(2) ?
C22 C21 C31 118.7(2) ?
C29 C21 C31 123.3(2) ?
C21 C22 O1 119.9(2) ?
C21 C22 C23 122.8(2) ?
O1 C22 C23 117.0(2) ?
C24 C23 C22 119.6(3) ?
C24 C23 H23 123.2(18) ?
C22 C23 H23 117.2(18) ?
C23 C24 C30 121.1(3) ?
C23 C24 H24 119.2(19) ?
C30 C24 H24 119.6(19) ?
C26 C25 C30 121.5(3) ?
C26 C25 H25 120(2) ?
C30 C25 H25 118(2) ?
C25 C26 C27 120.7(3) ?
C25 C26 H26 125(2) ?
C27 C26 H26 115(2) ?
C28 C27 C26 120.2(3) ?
C28 C27 H27 118(3) ?
C26 C27 H27 121(3) ?
C27 C28 C29 120.6(3) ?
C27 C28 H28 120.8(18) ?
C29 C28 H28 118.6(17) ?
C28 C29 C30 118.1(2) ?
C28 C29 C21 122.2(2) ?
C30 C29 C21 119.7(2) ?
C25 C30 C24 122.2(3) ?
C25 C30 C29 118.8(3) ?
C24 C30 C29 118.9(2) ?
C32 C31 C39 117.9(2) ?
C32 C31 C21 120.3(2) ?
C39 C31 C21 121.2(2) ?
C31 C32 O2 121.8(2) ?
C31 C32 C33 122.7(2) ?
O2 C32 C33 114.9(2) ?
C34 C33 C32 119.5(3) ?
C34 C33 H33 119.4(18) ?
C32 C33 H33 121.1(18) ?
C33 C34 C40 121.0(3) ?
C33 C34 H34 118.5(17) ?
C40 C34 H34 120.6(17) ?
C36 C35 C40 121.3(3) ?
C36 C35 H35 121.6(17) ?
C40 C35 H35 117.1(17) ?
C35 C36 C37 120.2(3) ?
C35 C36 H36 119(2) ?
C37 C36 H36 120(2) ?
C38 C37 C36 120.7(3) ?
C38 C37 H37 121(2) ?
C36 C37 H37 118(2) ?
C37 C38 C39 121.0(3) ?
C37 C38 H38 120.8(15) ?
C39 C38 H38 118.0(15) ?
C38 C39 C40 118.1(2) ?
C38 C39 C31 122.4(2) ?
C40 C39 C31 119.4(2) ?
C34 C40 C35 122.1(3) ?
C34 C40 C39 119.3(2) ?
C35 C40 C39 118.6(2) ?
N41 C41 O2 119.2(2) ?
N41 C41 C42 125.1(2) ?
O2 C41 C42 115.6(2) ?
C43 C42 C41 117.4(3) ?
C43 C42 H42 121(2) ?
C41 C42 H42 121(2) ?
C42 C43 C44 118.1(3) ?
C42 C43 H43 123(2) ?
C44 C43 H43 119(2) ?
C43 C44 C45 120.5(3) ?
C43 C44 N42 119.8(3) ?
C45 C44 N42 119.7(3) ?
N41 C45 C44 121.8(3) ?
N41 C45 H45 115.9(19) ?
C44 C45 H45 122.3(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C11 . 1.321(3) yes
N11 C15 . 1.336(4) yes
N12 O11 . 1.213(5) yes
N12 O12 . 1.221(5) yes
N12 C14 . 1.462(4) yes
N41 C41 . 1.312(3) yes
N41 C45 . 1.335(4) yes
N42 O41 . 1.219(4) yes
N42 O42 . 1.222(4) yes
N42 C44 . 1.458(4) yes
O1 C11 . 1.362(3) yes
O1 C22 . 1.398(3) yes
O2 C41 . 1.363(3) yes
O2 C32 . 1.403(3) yes
C11 C12 . 1.379(4) ?
C12 C13 . 1.344(5) ?
C12 H12 . 0.94(4) ?
C13 C14 . 1.382(5) ?
C13 H13 . 0.93(4) ?
C14 C15 . 1.368(4) ?
C15 H15 . 0.97(4) ?
C21 C22 . 1.377(3) ?
C21 C29 . 1.427(3) ?
C21 C31 . 1.493(4) yes
C22 C23 . 1.402(4) ?
C23 C24 . 1.355(4) ?
C23 H23 . 0.96(3) ?
C24 C30 . 1.415(4) ?
C24 H24 . 0.97(4) ?
C25 C26 . 1.343(5) ?
C25 C30 . 1.405(4) ?
C25 H25 . 1.02(4) ?
C26 C27 . 1.397(6) ?
C26 H26 . 0.91(4) ?
C27 C28 . 1.369(4) ?
C27 H27 . 0.87(4) ?
C28 C29 . 1.422(4) ?
C28 H28 . 0.99(3) ?
C29 C30 . 1.425(4) ?
C31 C32 . 1.375(3) ?
C31 C39 . 1.432(3) ?
C32 C33 . 1.406(4) ?
C33 C34 . 1.358(4) ?
C33 H33 . 0.94(3) ?
C34 C40 . 1.408(4) ?
C34 H34 . 0.91(3) ?
C35 C36 . 1.348(5) ?
C35 C40 . 1.414(4) ?
C35 H35 . 0.93(3) ?
C36 C37 . 1.402(5) ?
C36 H36 . 0.90(4) ?
C37 C38 . 1.353(4) ?
C37 H37 . 0.87(3) ?
C38 C39 . 1.417(3) ?
C38 H38 . 1.02(3) ?
C39 C40 . 1.424(3) ?
C41 C42 . 1.386(4) ?
C42 C43 . 1.369(5) ?
C42 H42 . 0.97(4) ?
C43 C44 . 1.373(4) ?
C43 H43 . 0.95(4) ?
C44 C45 . 1.374(4) ?
C45 H45 . 0.98(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131732
