#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023948.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_4023948
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             2006-09-19T14:55:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.839(4)
_cell_angle_beta                 82.749(4)
_cell_angle_gamma                86.109(4)
_cell_formula_units_Z            2
_cell_length_a                   6.7400(5)
_cell_length_b                   8.9687(7)
_cell_length_c                   16.8973(11)
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     1010.7(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_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    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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 Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.522855E-1
_diffrn_orient_matrix_UB_12      0.95716E-1
_diffrn_orient_matrix_UB_13      0.16717E-1
_diffrn_orient_matrix_UB_21      -0.134165
_diffrn_orient_matrix_UB_22      0.308812E-1
_diffrn_orient_matrix_UB_23      0.30185E-1
_diffrn_orient_matrix_UB_31      0.417919E-1
_diffrn_orient_matrix_UB_32      -0.487974E-1
_diffrn_orient_matrix_UB_33      0.486874E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.059
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5931
_diffrn_reflns_theta_full        24.93
_diffrn_reflns_theta_max         24.93
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.033(10)
_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     303
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1149P)²+0.3207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2226
_reflns_number_gt                2110
_reflns_number_total             3448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070318asi20070215_025019.cif
_cod_data_source_block           struct
_cod_original_formula_sum        'C22 H19 N1 O6'
_cod_database_code               4023948
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
O25 O 0.8237(3) -0.1269(3) 1.01502(14) 0.0619(6) Uani 1 1 d . . .
O26 O 0.8814(3) 0.0332(3) 0.91576(14) 0.0658(7) Uani 1 1 d . . .
H26 H 0.9713 0.0553 0.9413 0.099 Uiso 1 1 calc R . .
O28 O 0.0442(3) -0.4068(3) 0.91518(14) 0.0712(7) Uani 1 1 d . . .
N17 N 0.3248(4) 0.0111(3) 0.74966(17) 0.0672(8) Uani 1 1 d . . .
C23 C 0.4890(4) -0.2229(3) 0.9489(2) 0.0510(8) Uani 1 1 d . . .
O29 O 0.2246(4) -0.4228(3) 1.01642(16) 0.0803(8) Uani 1 1 d . . .
H29 H 0.1325 -0.4721 1.0351 0.12 Uiso 1 1 calc R . .
C18 C 0.3846(5) -0.0701(3) 0.81394(18) 0.0543(8) Uani 1 1 d . . .
C21 C 0.6054(4) -0.1128(3) 0.91497(18) 0.0492(7) Uani 1 1 d . . .
C27 C 0.1872(4) -0.3711(3) 0.94953(19) 0.0546(8) Uani 1 1 d . . .
C20 C 0.5555(5) -0.0389(4) 0.84807(19) 0.0545(8) Uani 1 1 d . . .
C19 C 0.2708(5) -0.1835(4) 0.84696(19) 0.0541(8) Uani 1 1 d . . .
C8 C 0.4074(5) 0.1522(4) 0.7317(2) 0.0591(8) Uani 1 1 d . . .
C24 C 0.7822(4) -0.0694(3) 0.95236(19) 0.0502(8) Uani 1 1 d . . .
C22 C 0.3211(4) -0.2576(3) 0.91366(18) 0.0503(8) Uani 1 1 d . . .
O2 O 0.7093(5) 0.5380(3) 0.68828(18) 0.0988(10) Uani 1 1 d . . .
C16 C 0.2355(5) -0.0646(4) 0.68952(19) 0.0613(9) Uani 1 1 d . . .
C3 C 0.6018(6) 0.4123(4) 0.7053(2) 0.0714(10) Uani 1 1 d . . .
C7 C 0.3990(7) 0.2596(4) 0.7908(3) 0.0808(12) Uani 1 1 d . . .
C6 C 0.5071(6) 0.1796(4) 0.6575(2) 0.0712(10) Uani 1 1 d . . .
C5 C 0.6030(6) 0.3105(5) 0.6445(2) 0.0775(11) Uani 1 1 d . . .
C14 C 0.0592(7) -0.0103(6) 0.6665(3) 0.0835(12) Uani 1 1 d . . .
O10 O 0.0144(6) -0.3045(6) 0.5133(2) 0.1392(15) Uani 1 1 d . . .
C15 C 0.3293(7) -0.1953(6) 0.6538(3) 0.0844(12) Uani 1 1 d . . .
C4 C 0.4977(7) 0.3894(4) 0.7778(3) 0.0834(12) Uani 1 1 d . . .
C11 C 0.0808(8) -0.2204(6) 0.5737(2) 0.0932(15) Uani 1 1 d . . .
C12 C 0.2545(8) -0.2694(6) 0.5970(3) 0.1024(15) Uani 1 1 d . . .
H12 H 0.3236 -0.3555 0.5736 0.123 Uiso 1 1 calc R . .
C13 C -0.0237(6) -0.0892(7) 0.6059(3) 0.1017(16) Uani 1 1 d . . .
H13 H -0.1435 -0.0543 0.5885 0.122 Uiso 1 1 calc R . .
C1 C 0.8078(9) 0.5931(6) 0.7489(3) 0.1194(19) Uani 1 1 d . . .
H1A H 0.7147 0.6095 0.7966 0.179 Uiso 1 1 calc R . .
H1B H 0.8625 0.6858 0.733 0.179 Uiso 1 1 calc R . .
H1C H 0.9143 0.5221 0.7589 0.179 Uiso 1 1 calc R . .
C9 C -0.1715(8) -0.2834(9) 0.4948(4) 0.152(3) Uani 1 1 d . . .
H9A H -0.2399 -0.2001 0.5256 0.228 Uiso 1 1 calc R . .
H9B H -0.2418 -0.3716 0.5066 0.228 Uiso 1 1 calc R . .
H9C H -0.1668 -0.2632 0.439 0.228 Uiso 1 1 calc R . .
H19 H 0.152(5) -0.207(3) 0.8241(18) 0.057(8) Uiso 1 1 d . . .
H20 H 0.635(5) 0.031(4) 0.827(2) 0.071(10) Uiso 1 1 d . . .
H23 H 0.514(5) -0.262(4) 0.997(2) 0.059(9) Uiso 1 1 d . . .
H6 H 0.514(6) 0.102(4) 0.613(2) 0.087(12) Uiso 1 1 d . . .
H7 H 0.338(6) 0.251(4) 0.843(3) 0.086(12) Uiso 1 1 d . . .
H5 H 0.667(6) 0.338(4) 0.588(3) 0.096(13) Uiso 1 1 d . . .
H14 H -0.001(7) 0.072(5) 0.690(3) 0.101(16) Uiso 1 1 d . . .
H4 H 0.507(6) 0.461(5) 0.821(3) 0.102(14) Uiso 1 1 d . . .
H15 H 0.432(8) -0.251(6) 0.678(3) 0.14(2) Uiso 1 1 d . . .
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
C24 O26 H26 109.5 . . ?
C18 N17 C16 119.1(3) . . ?
C18 N17 C8 119.2(3) . . ?
C16 N17 C8 119.0(3) . . ?
C21 C23 C22 118.2(3) . . ?
C21 C23 H23 120(2) . . ?
C22 C23 H23 122(2) . . ?
C27 O29 H29 109.5 . . ?
C20 C18 C19 117.8(3) . . ?
C20 C18 N17 121.7(3) . . ?
C19 C18 N17 120.5(3) . . ?
C20 C21 C23 120.9(3) . . ?
C20 C21 C24 119.3(3) . . ?
C23 C21 C24 119.8(3) . . ?
O28 C27 O29 123.7(3) . . ?
O28 C27 C22 119.6(3) . . ?
O29 C27 C22 116.6(3) . . ?
C21 C20 C18 121.1(3) . . ?
C21 C20 H20 118(2) . . ?
C18 C20 H20 120(2) . . ?
C22 C19 C18 120.9(3) . . ?
C22 C19 H19 119.8(19) . . ?
C18 C19 H19 119.2(19) . . ?
C7 C8 C6 118.5(3) . . ?
C7 C8 N17 119.6(3) . . ?
C6 C8 N17 121.7(3) . . ?
O25 C24 O26 124.1(3) . . ?
O25 C24 C21 120.9(3) . . ?
O26 C24 C21 114.9(3) . . ?
C19 C22 C23 120.9(3) . . ?
C19 C22 C27 118.7(3) . . ?
C23 C22 C27 120.3(3) . . ?
C1 O2 C3 116.8(3) . . ?
C14 C16 C15 119.1(4) . . ?
C14 C16 N17 121.0(4) . . ?
C15 C16 N17 119.9(3) . . ?
C4 C3 C5 120.0(3) . . ?
C4 C3 O2 123.3(4) . . ?
C5 C3 O2 116.7(3) . . ?
C8 C7 C4 120.9(4) . . ?
C8 C7 H7 125(2) . . ?
C4 C7 H7 114(2) . . ?
C8 C6 C5 120.3(4) . . ?
C8 C6 H6 120(2) . . ?
C5 C6 H6 120(2) . . ?
C3 C5 C6 120.2(3) . . ?
C3 C5 H5 118(2) . . ?
C6 C5 H5 121(2) . . ?
C16 C14 C13 119.0(5) . . ?
C16 C14 H14 119(3) . . ?
C13 C14 H14 122(3) . . ?
C9 O10 C11 121.6(5) . . ?
C12 C15 C16 122.5(5) . . ?
C12 C15 H15 115(3) . . ?
C16 C15 H15 121(3) . . ?
C3 C4 C7 119.9(4) . . ?
C3 C4 H4 118(3) . . ?
C7 C4 H4 122(3) . . ?
C12 C11 O10 116.1(5) . . ?
C12 C11 C13 121.5(4) . . ?
O10 C11 C13 122.4(5) . . ?
C15 C12 C11 120.0(5) . . ?
C15 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C11 C13 C14 117.9(4) . . ?
C11 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O10 C9 H9A 109.5 . . ?
O10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O25 C24 1.240(4) . ?
O26 C24 1.293(3) . ?
O26 H26 0.82 . ?
O28 C27 1.243(4) . ?
N17 C18 1.403(4) . ?
N17 C16 1.430(4) . ?
N17 C8 1.438(4) . ?
C23 C21 1.389(4) . ?
C23 C22 1.395(4) . ?
C23 H23 0.92(4) . ?
O29 C27 1.276(4) . ?
O29 H29 0.82 . ?
C18 C20 1.394(4) . ?
C18 C19 1.396(4) . ?
C21 C20 1.385(5) . ?
C21 C24 1.489(4) . ?
C27 C22 1.491(4) . ?
C20 H20 0.90(4) . ?
C19 C22 1.384(5) . ?
C19 H19 0.97(3) . ?
C8 C7 1.370(5) . ?
C8 C6 1.380(5) . ?
O2 C1 1.391(5) . ?
O2 C3 1.395(4) . ?
C16 C14 1.358(5) . ?
C16 C15 1.386(6) . ?
C3 C4 1.359(5) . ?
C3 C5 1.363(5) . ?
C7 C4 1.386(5) . ?
C7 H7 0.94(4) . ?
C6 C5 1.385(5) . ?
C6 H6 1.01(4) . ?
C5 H5 1.04(4) . ?
C14 C13 1.428(6) . ?
C14 H14 0.88(4) . ?
O10 C9 1.331(6) . ?
O10 C11 1.396(5) . ?
C15 C12 1.329(6) . ?
C15 H15 0.96(6) . ?
C4 H4 0.97(4) . ?
C11 C12 1.331(7) . ?
C11 C13 1.396(7) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20564041
