#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/78/4307899.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_4307899
loop_
_publ_author_name
'Aramice Y. S. Malkhasian'
'Maila E. Finch'
'Borislava Nikolovski'
'Adarsh Menon'
'Benjamin E. Kucera'
'Ferman A. Chavez'
_publ_section_title
;
N,N'-Dimethylformamide-Derived Products from Catalytic Oxidation of
3-Hydroxyflavone
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2950
_journal_page_last               2952
_journal_paper_doi               10.1021/ic062408o
_journal_volume                  46
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_chemical_name_common            06123
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7252(13)
_cell_length_b                   11.5021(17)
_cell_length_c                   13.944(2)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.80
_cell_measurement_theta_min      2.30
_cell_volume                     1399.4(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6947
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
'Flack H D (1983), 1027 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0482
_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)+(0.0640P)²+0.7234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                1258
_reflns_number_total             1441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic062408o-file001_1.cif
_cod_data_source_block           06123
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4307899
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O -0.0824(3) 1.0262(2) 0.3974(2) 0.0458(7) Uani 1 1 d . . .
O2 O -0.0839(3) 0.9907(2) 0.55200(18) 0.0360(6) Uani 1 1 d . . .
O3 O 0.2205(3) 0.7271(2) 0.5097(2) 0.0393(7) Uani 1 1 d . . .
N1 N 0.1676(4) 0.8741(3) 0.3581(2) 0.0337(7) Uani 1 1 d . . .
C1 C -0.0185(4) 0.9782(3) 0.4636(3) 0.0336(8) Uani 1 1 d . . .
C2 C -0.0429(4) 0.9165(3) 0.6271(3) 0.0321(8) Uani 1 1 d . . .
C3 C -0.1226(4) 0.9335(4) 0.7123(3) 0.0406(10) Uani 1 1 d . . .
H3 H -0.1973 0.9932 0.7175 0.049 Uiso 1 1 calc R . .
C4 C -0.0909(5) 0.8620(4) 0.7889(3) 0.0485(11) Uani 1 1 d . . .
H4 H -0.1419 0.8744 0.8482 0.058 Uiso 1 1 calc R . .
C5 C 0.0143(5) 0.7722(4) 0.7809(3) 0.0485(11) Uani 1 1 d . . .
H5 H 0.0331 0.7223 0.8339 0.058 Uiso 1 1 calc R . .
C6 C 0.0915(5) 0.7555(3) 0.6956(3) 0.0408(10) Uani 1 1 d . . .
H6 H 0.1635 0.6939 0.6900 0.049 Uiso 1 1 calc R . .
C7 C 0.0645(4) 0.8287(3) 0.6173(2) 0.0300(8) Uani 1 1 d . . .
C8 C 0.1444(4) 0.8111(3) 0.5255(3) 0.0293(8) Uani 1 1 d . . .
C9 C 0.1339(4) 0.9156(3) 0.4544(2) 0.0283(8) Uani 1 1 d . . .
C10 C 0.0540(5) 0.7929(4) 0.3207(3) 0.0426(10) Uani 1 1 d . . .
H10A H 0.0322 0.7334 0.3692 0.064 Uiso 1 1 calc R . .
H10B H 0.0939 0.7557 0.2626 0.064 Uiso 1 1 calc R . .
H10C H -0.0405 0.8350 0.3053 0.064 Uiso 1 1 calc R . .
C11 C 0.2056(5) 0.9639(4) 0.2861(3) 0.0433(10) Uani 1 1 d . . .
H11A H 0.2863 1.0146 0.3114 0.065 Uiso 1 1 calc R . .
H11B H 0.1141 1.0103 0.2720 0.065 Uiso 1 1 calc R . .
H11C H 0.2417 0.9264 0.2272 0.065 Uiso 1 1 calc R . .
C12 C 0.2631(4) 0.9978(3) 0.4901(2) 0.0261(7) Uani 1 1 d . . .
C13 C 0.4103(4) 0.9530(3) 0.4939(3) 0.0312(8) Uani 1 1 d . . .
H13 H 0.4284 0.8753 0.4737 0.037 Uiso 1 1 calc R . .
C14 C 0.5315(4) 1.0199(3) 0.5269(3) 0.0374(9) Uani 1 1 d . . .
H14 H 0.6317 0.9879 0.5302 0.045 Uiso 1 1 calc R . .
C15 C 0.5059(5) 1.1321(3) 0.5545(3) 0.0390(9) Uani 1 1 d . . .
H15 H 0.5886 1.1780 0.5776 0.047 Uiso 1 1 calc R . .
C16 C 0.3606(5) 1.1793(3) 0.5491(3) 0.0387(9) Uani 1 1 d . . .
H16 H 0.3439 1.2577 0.5677 0.046 Uiso 1 1 calc R . .
C17 C 0.2387(4) 1.1121(3) 0.5165(3) 0.0322(8) Uani 1 1 d . . .
H17 H 0.1389 1.1447 0.5123 0.039 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 O2 C2 120.3(3) . . ?
C9 N1 C10 113.7(3) . . ?
C9 N1 C11 116.2(3) . . ?
C10 N1 C11 111.0(3) . . ?
O1 C1 O2 116.6(3) . . ?
O1 C1 C9 123.7(3) . . ?
O2 C1 C9 119.5(3) . . ?
C7 C2 C3 121.8(4) . . ?
C7 C2 O2 123.0(3) . . ?
C3 C2 O2 115.2(3) . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 118.4(3) . . ?
C2 C7 C8 120.5(3) . . ?
C6 C7 C8 121.1(3) . . ?
O3 C8 C7 122.4(3) . . ?
O3 C8 C9 122.6(3) . . ?
C7 C8 C9 114.8(3) . . ?
N1 C9 C1 114.2(3) . . ?
N1 C9 C12 110.4(3) . . ?
C1 C9 C12 108.7(3) . . ?
N1 C9 C8 108.7(3) . . ?
C1 C9 C8 111.3(3) . . ?
C12 C9 C8 102.8(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 C9 123.5(3) . . ?
C13 C12 C9 117.4(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.9(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
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
O1 C1 1.211(4) . ?
O2 C1 1.366(4) . ?
O2 C2 1.398(4) . ?
O3 C8 1.194(4) . ?
N1 C9 1.457(5) . ?
N1 C10 1.457(5) . ?
N1 C11 1.478(5) . ?
C1 C9 1.517(5) . ?
C2 C7 1.384(5) . ?
C2 C3 1.389(5) . ?
C3 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.471(5) . ?
C8 C9 1.561(5) . ?
C9 C12 1.553(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.382(5) . ?
C12 C13 1.384(4) . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.365(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
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
C2 O2 C1 O1 163.7(3) . . . . ?
C2 O2 C1 C9 -21.5(4) . . . . ?
C1 O2 C2 C7 0.6(5) . . . . ?
C1 O2 C2 C3 -176.8(3) . . . . ?
C7 C2 C3 C4 1.2(5) . . . . ?
O2 C2 C3 C4 178.6(3) . . . . ?
C2 C3 C4 C5 -2.2(6) . . . . ?
C3 C4 C5 C6 1.6(6) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C3 C2 C7 C6 0.4(5) . . . . ?
O2 C2 C7 C6 -176.8(3) . . . . ?
C3 C2 C7 C8 178.6(3) . . . . ?
O2 C2 C7 C8 1.4(5) . . . . ?
C5 C6 C7 C2 -1.0(5) . . . . ?
C5 C6 C7 C8 -179.2(3) . . . . ?
C2 C7 C8 O3 -168.9(3) . . . . ?
C6 C7 C8 O3 9.2(5) . . . . ?
C2 C7 C8 C9 16.3(4) . . . . ?
C6 C7 C8 C9 -165.5(3) . . . . ?
C10 N1 C9 C1 -59.2(4) . . . . ?
C11 N1 C9 C1 71.6(4) . . . . ?
C10 N1 C9 C12 177.9(3) . . . . ?
C11 N1 C9 C12 -51.3(4) . . . . ?
C10 N1 C9 C8 65.8(4) . . . . ?
C11 N1 C9 C8 -163.5(3) . . . . ?
O1 C1 C9 N1 -24.8(5) . . . . ?
O2 C1 C9 N1 160.8(3) . . . . ?
O1 C1 C9 C12 99.0(4) . . . . ?
O2 C1 C9 C12 -75.4(4) . . . . ?
O1 C1 C9 C8 -148.4(3) . . . . ?
O2 C1 C9 C8 37.2(4) . . . . ?
O3 C8 C9 N1 25.1(5) . . . . ?
C7 C8 C9 N1 -160.1(3) . . . . ?
O3 C8 C9 C1 151.8(3) . . . . ?
C7 C8 C9 C1 -33.4(4) . . . . ?
O3 C8 C9 C12 -92.0(4) . . . . ?
C7 C8 C9 C12 82.8(3) . . . . ?
N1 C9 C12 C17 120.5(3) . . . . ?
C1 C9 C12 C17 -5.5(5) . . . . ?
C8 C9 C12 C17 -123.6(3) . . . . ?
N1 C9 C12 C13 -58.5(4) . . . . ?
C1 C9 C12 C13 175.4(3) . . . . ?
C8 C9 C12 C13 57.3(4) . . . . ?
C17 C12 C13 C14 2.3(5) . . . . ?
C9 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 -1.1(6) . . . . ?
C13 C14 C15 C16 -0.5(6) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C13 C12 C17 C16 -2.0(5) . . . . ?
C9 C12 C17 C16 179.0(3) . . . . ?
C15 C16 C17 C12 0.5(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21177222
