#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023947.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_4023947
loop_
_publ_author_name
'Hidenori Murata'
'Paul M. Lahti'
_publ_contact_author_address
;
Department of Chemistry, University of Massachusetts, Amherst, MA 01003 USA
;
_publ_contact_author_email       'lahti@chem.umass.edu '
_publ_contact_author_fax         '1-413-545-4490 '
_publ_contact_author_name        'Hidenori Murata, Paul M. Lahti'
_publ_contact_author_phone       1-413-545-4890
_publ_section_title
;
 Synthesis and Oxidation of Triarylamine Derivatives Bearing
 Hydrogen-Bonding Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4974
_journal_page_last               4977
_journal_paper_doi               10.1021/jo070318a
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H19 N1 O6'
_chemical_formula_sum            'C22 H19 N O6'
_chemical_formula_weight         393.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-09-29T13:37:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                91.8910(10)
_cell_angle_beta                 108.2540(10)
_cell_angle_gamma                93.9190(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6333(2)
_cell_length_b                   10.7971(2)
_cell_length_c                   12.4742(3)
_cell_measurement_reflns_used    5221
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     1227.26(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.689889E-1
_diffrn_orient_matrix_UB_12      0.92477E-2
_diffrn_orient_matrix_UB_13      0.44694E-1
_diffrn_orient_matrix_UB_21      0.4439E-3
_diffrn_orient_matrix_UB_22      0.909661E-1
_diffrn_orient_matrix_UB_23      -0.127226E-1
_diffrn_orient_matrix_UB_31      -0.852708E-1
_diffrn_orient_matrix_UB_32      -0.169233E-1
_diffrn_orient_matrix_UB_33      -0.706385E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.056
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9842
_diffrn_reflns_theta_full        27.2
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          2
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.33
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.027(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1385P)²+0.0617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2456
_reflns_number_gt                2788
_reflns_number_total             5379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070318asi20070215_024952.cif
_cod_data_source_block           struct
_cod_original_formula_sum        'C22 H19 N1 O6'
_cod_database_code               4023947
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.5565(2) -0.39683(16) 0.41219(17) 0.0746(6) Uani 1 1 d . . .
H6 H 0.5243 -0.4673 0.4194 0.112 Uiso 1 1 calc R . .
O5 O 0.5337(2) -0.36789(17) 0.58253(17) 0.0775(6) Uani 1 1 d . . .
O4 O 0.6525(2) 0.04668(18) 0.77842(16) 0.0803(6) Uani 1 1 d . . .
H4 H 0.6299 -0.0282 0.7653 0.12 Uiso 1 1 calc R . .
O2 O 0.9603(2) 0.51742(18) 0.3464(2) 0.0895(7) Uani 1 1 d . . .
O3 O 0.7272(2) 0.20338(17) 0.69403(17) 0.0787(6) Uani 1 1 d . . .
O1 O 0.8318(3) -0.2834(3) -0.02033(19) 0.1093(9) Uani 1 1 d . . .
N1 N 0.7641(2) 0.01752(19) 0.32822(19) 0.0637(6) Uani 1 1 d . . .
C3 C 0.6847(2) 0.0040(2) 0.6002(2) 0.0499(6) Uani 1 1 d . . .
C1 C 0.6312(2) -0.1183(2) 0.5965(2) 0.0513(6) Uani 1 1 d . . .
H1 H 0.6021 -0.1485 0.6558 0.062 Uiso 1 1 calc R . .
C6 C 0.7207(2) -0.0285(2) 0.4172(2) 0.0510(6) Uani 1 1 d . . .
C2 C 0.6214(2) -0.1960(2) 0.5026(2) 0.0495(6) Uani 1 1 d . . .
C4 C 0.6634(2) -0.1518(2) 0.4138(2) 0.0524(6) Uani 1 1 d . . .
H4A H 0.6536 -0.2046 0.351 0.063 Uiso 1 1 calc R . .
C5 C 0.7302(2) 0.0486(2) 0.5122(2) 0.0520(6) Uani 1 1 d . . .
H5 H 0.7675 0.131 0.5165 0.062 Uiso 1 1 calc R . .
C13 C 0.8162(3) 0.1458(2) 0.3327(2) 0.0557(6) Uani 1 1 d . . .
C7 C 0.7787(3) -0.0614(2) 0.2385(2) 0.0587(7) Uani 1 1 d . . .
C19 C 0.5661(3) -0.3276(2) 0.4999(2) 0.0528(6) Uani 1 1 d . . .
C20 C 0.6904(3) 0.0916(2) 0.6963(2) 0.0593(7) Uani 1 1 d . . .
C9 C 0.7129(4) -0.0343(3) 0.1294(3) 0.0810(9) Uani 1 1 d . . .
H9 H 0.6548 0.0324 0.1146 0.097 Uiso 1 1 calc R . .
C14 C 0.9632(3) 0.1791(3) 0.3592(3) 0.0671(7) Uani 1 1 d . . .
H14 H 1.029 0.1179 0.3749 0.08 Uiso 1 1 calc R . .
C18 C 0.9201(3) 0.3933(2) 0.3416(2) 0.0638(7) Uani 1 1 d . . .
C15 C 0.7201(3) 0.2374(3) 0.3094(3) 0.0681(8) Uani 1 1 d . . .
H15 H 0.6198 0.2161 0.2904 0.082 Uiso 1 1 calc R . .
C16 C 1.0158(3) 0.3024(3) 0.3632(3) 0.0715(8) Uani 1 1 d . . .
H16 H 1.1159 0.3233 0.3805 0.086 Uiso 1 1 calc R . .
C17 C 0.7712(3) 0.3599(3) 0.3140(3) 0.0728(8) Uani 1 1 d . . .
H17 H 0.7053 0.421 0.2984 0.087 Uiso 1 1 calc R . .
C8 C 0.8616(3) -0.1629(3) 0.2589(2) 0.0733(8) Uani 1 1 d . . .
H8 H 0.9081 -0.1826 0.3329 0.088 Uiso 1 1 calc R . .
C11 C 0.7304(4) -0.1038(3) 0.0394(3) 0.0856(9) Uani 1 1 d . . .
H11 H 0.6883 -0.0817 -0.0345 0.103 Uiso 1 1 calc R . .
C12 C 0.8107(4) -0.2051(3) 0.0613(3) 0.0763(8) Uani 1 1 d . . .
C22 C 1.1130(4) 0.5546(3) 0.3764(4) 0.1013(12) Uani 1 1 d . . .
H22A H 1.163 0.5247 0.4489 0.152 Uiso 1 1 calc R . .
H22B H 1.1273 0.6437 0.3798 0.152 Uiso 1 1 calc R . .
H22C H 1.1516 0.5204 0.3207 0.152 Uiso 1 1 calc R . .
C10 C 0.8755(4) -0.2350(3) 0.1703(3) 0.0814(9) Uani 1 1 d . . .
H10 H 0.9292 -0.3044 0.1847 0.098 Uiso 1 1 calc R . .
C26 C 0.3374(4) -0.2061(3) 0.0562(3) 0.0889(10) Uani 1 1 d . A .
C21 C 0.7729(7) -0.2548(5) -0.1354(3) 0.159(2) Uani 1 1 d . . .
H21A H 0.7959 -0.3166 -0.1828 0.238 Uiso 1 1 calc R . .
H21B H 0.8146 -0.1746 -0.1461 0.238 Uiso 1 1 calc R . .
H21C H 0.6683 -0.2537 -0.155 0.238 Uiso 1 1 calc R . .
O7A O 0.2985(9) -0.3619(7) 0.1515(6) 0.097(4) Uani 0.319(9) 1 d P A 1
O7B O 0.3511(13) -0.4101(11) 0.0347(14) 0.331(9) Uani 0.681(9) 1 d P A 2
C25 C 0.4280(6) -0.3127(6) 0.0903(8) 0.185(3) Uani 1 1 d . . .
C23 C 0.1919(7) -0.2584(7) -0.0036(6) 0.176(2) Uani 1 1 d . . .
C24 C 0.1843(7) -0.3856(7) 0.0180(10) 0.231(5) Uani 1 1 d . A .
loop_
_atom_type_symbol
_atom_type_number_in_cell
C 44
H 38
N 2
O 12
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
C19 O6 H6 109.5 . . ?
C20 O4 H4 109.5 . . ?
C18 O2 C22 117.4(2) . . ?
C12 O1 C21 118.4(3) . . ?
C6 N1 C7 122.7(2) . . ?
C6 N1 C13 119.8(2) . . ?
C7 N1 C13 116.93(19) . . ?
C1 C3 C5 120.5(2) . . ?
C1 C3 C20 120.7(2) . . ?
C5 C3 C20 118.8(2) . . ?
C3 C1 C2 118.9(2) . . ?
C3 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
N1 C6 C4 121.5(2) . . ?
N1 C6 C5 120.8(2) . . ?
C4 C6 C5 117.7(2) . . ?
C4 C2 C1 120.9(2) . . ?
C4 C2 C19 120.4(2) . . ?
C1 C2 C19 118.7(2) . . ?
C2 C4 C6 120.8(2) . . ?
C2 C4 H4A 119.6 . . ?
C6 C4 H4A 119.6 . . ?
C3 C5 C6 121.1(2) . . ?
C3 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C14 C13 C15 118.8(2) . . ?
C14 C13 N1 120.3(2) . . ?
C15 C13 N1 120.9(2) . . ?
C9 C7 C8 118.5(3) . . ?
C9 C7 N1 119.3(3) . . ?
C8 C7 N1 122.1(2) . . ?
O5 C19 O6 122.5(2) . . ?
O5 C19 C2 119.8(2) . . ?
O6 C19 C2 117.6(2) . . ?
O3 C20 O4 122.6(2) . . ?
O3 C20 C3 120.0(2) . . ?
O4 C20 C3 117.4(2) . . ?
C7 C9 C11 121.6(3) . . ?
C7 C9 H9 119.2 . . ?
C11 C9 H9 119.2 . . ?
C13 C14 C16 121.2(2) . . ?
C13 C14 H14 119.4 . . ?
C16 C14 H14 119.4 . . ?
O2 C18 C16 124.6(2) . . ?
O2 C18 C17 116.2(2) . . ?
C16 C18 C17 119.1(2) . . ?
C17 C15 C13 120.4(2) . . ?
C17 C15 H15 119.8 . . ?
C13 C15 H15 119.8 . . ?
C18 C16 C14 119.9(2) . . ?
C18 C16 H16 120.1 . . ?
C14 C16 H16 120.1 . . ?
C15 C17 C18 120.6(2) . . ?
C15 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C10 C8 C7 120.3(3) . . ?
C10 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C12 C11 C9 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C9 C11 H11 120.5 . . ?
C10 C12 C11 120.2(3) . . ?
C10 C12 O1 115.4(3) . . ?
C11 C12 O1 124.5(3) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C10 C8 120.3(3) . . ?
C12 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
C23 C26 C25 106.3(5) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 O7A C25 85.3(6) . . ?
C25 O7B C24 105.7(6) . . ?
O7B C25 C26 106.7(7) . . ?
O7B C25 O7A 70.0(8) . . ?
C26 C25 O7A 85.0(4) . . ?
C24 C23 C26 107.7(6) . . ?
C23 C24 O7B 98.5(7) . . ?
C23 C24 O7A 93.4(6) . . ?
O7B C24 O7A 64.8(6) . . ?
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
O6 C19 1.279(3) . ?
O6 H6 0.82 . ?
O5 C19 1.250(3) . ?
O4 C20 1.288(3) . ?
O4 H4 0.82 . ?
O2 C18 1.364(3) . ?
O2 C22 1.424(4) . ?
O3 C20 1.239(3) . ?
O1 C12 1.374(4) . ?
O1 C21 1.422(5) . ?
N1 C6 1.398(3) . ?
N1 C7 1.433(3) . ?
N1 C13 1.434(3) . ?
C3 C1 1.378(3) . ?
C3 C5 1.392(3) . ?
C3 C20 1.487(4) . ?
C1 C2 1.394(3) . ?
C1 H1 0.93 . ?
C6 C4 1.400(3) . ?
C6 C5 1.400(3) . ?
C2 C4 1.381(3) . ?
C2 C19 1.479(3) . ?
C4 H4A 0.93 . ?
C5 H5 0.93 . ?
C13 C14 1.369(4) . ?
C13 C15 1.377(4) . ?
C7 C9 1.361(4) . ?
C7 C8 1.383(4) . ?
C9 C11 1.389(4) . ?
C9 H9 0.93 . ?
C14 C16 1.385(4) . ?
C14 H14 0.93 . ?
C18 C16 1.368(4) . ?
C18 C17 1.384(4) . ?
C15 C17 1.373(4) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C8 C10 1.377(4) . ?
C8 H8 0.93 . ?
C11 C12 1.368(4) . ?
C11 H11 0.93 . ?
C12 C10 1.367(4) . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
C10 H10 0.93 . ?
C26 C23 1.432(7) . ?
C26 C25 1.485(7) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
O7A C24 1.684(12) . ?
O7A C25 1.719(11) . ?
O7B C25 1.288(11) . ?
O7B C24 1.595(11) . ?
C23 C24 1.409(10) . ?
