#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:49:25 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179079 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/41/4304166.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_4304166
loop_
_publ_author_name
'Rupam Sarma'
'Anirban Karmakar'
'Jubaraj B. Baruah'
_publ_section_title
;
N-Oxides in Metal-Containing Multicomponent Molecular Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              763
_journal_page_last               765
_journal_paper_doi               10.1021/ic701639n
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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                106.374(13)
_cell_angle_beta                 91.195(13)
_cell_angle_gamma                115.567(12)
_cell_formula_units_Z            2
_cell_length_a                   7.7728(14)
_cell_length_b                   8.3094(17)
_cell_length_c                   12.991(3)
_cell_measurement_temperature    296(2)
_cell_volume                     716.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1667
_diffrn_reflns_av_sigmaI/netI    0.1022
_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       -16
_diffrn_reflns_number            8628
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0943
_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)+(0.1960P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.3423
_reflns_number_gt                1508
_reflns_number_total             2893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic701639n-file004.cif
_cod_data_source_block           mntolqno_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_original_cell_volume        716.3(2)
_cod_database_code               4304166
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
C17 C 0.7341(4) 0.6139(4) 0.1010(2) 0.0619(9) Uani 1 1 d . . .
N1 N 0.7603(4) 0.7756(4) 0.07911(19) 0.0661(8) Uani 1 1 d . . .
O3 O 0.7600(3) 0.9184(3) 0.15833(17) 0.0813(8) Uani 1 1 d . . .
O2 O 0.0633(3) 0.0872(3) 0.30424(18) 0.0888(9) Uani 1 1 d . . .
H2 H -0.0359 0.0210 0.2593 0.133 Uiso 1 1 calc R . .
C12 C 0.7372(4) 0.4649(5) 0.0169(2) 0.0653(9) Uani 1 1 d . . .
C2 C 0.3651(5) 0.1129(4) 0.3634(2) 0.0657(9) Uani 1 1 d . . .
O1 O 0.1800(4) -0.0731(3) 0.18663(18) 0.0925(9) Uani 1 1 d . . .
C16 C 0.7084(5) 0.6015(4) 0.2052(2) 0.0728(10) Uani 1 1 d . . .
H16 H 0.7082 0.7010 0.2605 0.087 Uiso 1 1 calc R . .
C1 C 0.1961(5) 0.0333(5) 0.2752(2) 0.0682(10) Uani 1 1 d . . .
C15 C 0.6834(5) 0.4398(5) 0.2240(3) 0.0762(10) Uani 1 1 d . . .
H15 H 0.6646 0.4290 0.2927 0.091 Uiso 1 1 calc R . .
C9 C 0.7854(5) 0.7903(5) -0.0199(3) 0.0763(10) Uani 1 1 d . . .
H9 H 0.7999 0.8993 -0.0332 0.092 Uiso 1 1 calc R . .
C11 C 0.7685(4) 0.4866(5) -0.0861(2) 0.0782(11) Uani 1 1 d . . .
H11 H 0.7741 0.3908 -0.1418 0.094 Uiso 1 1 calc R . .
C7 C 0.3849(5) 0.2415(5) 0.4628(3) 0.0784(11) Uani 1 1 d . . .
H7 H 0.2872 0.2764 0.4784 0.094 Uiso 1 1 calc R . .
C3 C 0.5129(5) 0.0630(4) 0.3414(2) 0.0698(10) Uani 1 1 d . . .
H3A H 0.5018 -0.0231 0.2747 0.084 Uiso 1 1 calc R . .
C10 C 0.7903(5) 0.6456(5) -0.1033(3) 0.0802(11) Uani 1 1 d . . .
H10 H 0.8087 0.6589 -0.1715 0.096 Uiso 1 1 calc R . .
C13 C 0.7125(5) 0.3030(5) 0.0409(3) 0.0755(10) Uani 1 1 d . . .
H13 H 0.7144 0.2027 -0.0128 0.091 Uiso 1 1 calc R . .
C4 C 0.6755(5) 0.1407(5) 0.4183(3) 0.0758(10) Uani 1 1 d . . .
H4 H 0.7719 0.1037 0.4034 0.091 Uiso 1 1 calc R . .
C5 C 0.6987(5) 0.2726(5) 0.5173(3) 0.0774(10) Uani 1 1 d . . .
C14 C 0.6856(5) 0.2912(5) 0.1424(3) 0.0825(11) Uani 1 1 d . . .
H14 H 0.6686 0.1826 0.1571 0.099 Uiso 1 1 calc R . .
C6 C 0.5493(5) 0.3188(5) 0.5394(2) 0.0815(11) Uani 1 1 d . . .
H6 H 0.5595 0.4031 0.6067 0.098 Uiso 1 1 calc R . .
C8 C 0.8795(6) 0.3614(6) 0.6014(3) 0.1028(13) Uani 1 1 d . . .
H8A H 0.8467 0.3244 0.6647 0.154 Uiso 1 1 calc R . .
H8B H 0.9355 0.4962 0.6211 0.154 Uiso 1 1 calc R . .
H8C H 0.9710 0.3201 0.5715 0.154 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C17 C16 120.0(3) . . ?
N1 C17 C12 118.6(3) . . ?
C16 C17 C12 121.3(3) . . ?
O3 N1 C9 119.9(3) . . ?
O3 N1 C17 119.2(2) . . ?
C9 N1 C17 120.9(3) . . ?
C1 O2 H2 109.5 . . ?
C13 C12 C17 117.8(3) . . ?
C13 C12 C11 123.1(3) . . ?
C17 C12 C11 119.1(3) . . ?
C7 C2 C3 119.0(3) . . ?
C7 C2 C1 122.7(3) . . ?
C3 C2 C1 118.2(3) . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
O1 C1 O2 122.8(3) . . ?
O1 C1 C2 123.6(3) . . ?
O2 C1 C2 113.6(2) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N1 C9 C10 121.2(3) . . ?
N1 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C2 C7 C6 120.4(3) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C8 121.6(3) . . ?
C6 C5 C8 120.3(3) . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C17 N1 1.382(4) . ?
C17 C16 1.399(4) . ?
C17 C12 1.411(4) . ?
N1 O3 1.334(3) . ?
N1 C9 1.337(4) . ?
O2 C1 1.314(3) . ?
O2 H2 0.8200 . ?
C12 C13 1.400(5) . ?
C12 C11 1.411(4) . ?
C2 C7 1.381(4) . ?
C2 C3 1.390(4) . ?
C2 C1 1.495(5) . ?
O1 C1 1.203(3) . ?
C16 C15 1.365(4) . ?
C16 H16 0.9300 . ?
C15 C14 1.389(4) . ?
C15 H15 0.9300 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C11 C10 1.342(4) . ?
C11 H11 0.9300 . ?
C7 C6 1.383(5) . ?
C7 H7 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C10 H10 0.9300 . ?
C13 C14 1.363(5) . ?
C13 H13 0.9300 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(5) . ?
C5 C8 1.516(5) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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
C16 C17 N1 O3 -0.2(4) . . . . ?
C12 C17 N1 O3 -179.2(2) . . . . ?
C16 C17 N1 C9 179.9(3) . . . . ?
C12 C17 N1 C9 0.9(4) . . . . ?
N1 C17 C12 C13 179.3(2) . . . . ?
C16 C17 C12 C13 0.4(5) . . . . ?
N1 C17 C12 C11 0.6(4) . . . . ?
C16 C17 C12 C11 -178.4(2) . . . . ?
N1 C17 C16 C15 -179.8(3) . . . . ?
C12 C17 C16 C15 -0.9(5) . . . . ?
C7 C2 C1 O1 177.0(3) . . . . ?
C3 C2 C1 O1 0.8(6) . . . . ?
C7 C2 C1 O2 -4.5(5) . . . . ?
C3 C2 C1 O2 179.3(3) . . . . ?
C17 C16 C15 C14 0.8(5) . . . . ?
O3 N1 C9 C10 178.7(3) . . . . ?
C17 N1 C9 C10 -1.4(5) . . . . ?
C13 C12 C11 C10 179.7(3) . . . . ?
C17 C12 C11 C10 -1.6(5) . . . . ?
C3 C2 C7 C6 -0.2(5) . . . . ?
C1 C2 C7 C6 -176.4(3) . . . . ?
C7 C2 C3 C4 0.3(5) . . . . ?
C1 C2 C3 C4 176.6(3) . . . . ?
C12 C11 C10 C9 1.1(5) . . . . ?
N1 C9 C10 C11 0.4(5) . . . . ?
C17 C12 C13 C14 0.3(5) . . . . ?
C11 C12 C13 C14 179.0(3) . . . . ?
C2 C3 C4 C5 -1.6(6) . . . . ?
C3 C4 C5 C6 2.8(6) . . . . ?
C3 C4 C5 C8 -178.7(3) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C16 C15 C14 C13 -0.2(6) . . . . ?
C2 C7 C6 C5 1.4(6) . . . . ?
C4 C5 C6 C7 -2.7(6) . . . . ?
C8 C5 C6 C7 178.8(3) . . . . ?
