#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/23/4122308.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_4122308
loop_
_publ_author_name
'Rubinstein, Amir'
'Jiménez-Lozanao, Pablo'
'Carbó, Jorge J'
'Poblet, Josep M.'
'Neumann, Ronny'
_publ_section_title
;
 Aerobic carbon-carbon bond cleavage of alkenes to aldehydes catalyzed by
 first-row transition-metal-substituted polyoxometalates in the presence
 of nitrogen dioxide.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10941
_journal_page_last               10948
_journal_paper_doi               10.1021/ja502846h
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C18 H22 N O7, N O3'
_chemical_formula_sum            'C18 H22 N2 O10'
_chemical_formula_weight         426.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 127.290(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.015(2)
_cell_length_b                   14.1139(18)
_cell_length_c                   10.6266(14)
_cell_measurement_reflns_used    7706
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.15
_cell_volume                     1911.0(5)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'Collect package Bruker APEX-2'
_computing_data_reduction        'APEX 2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX - II KappaCCD'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6499
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELXL-97 (Sheldrick, 1997)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0361
_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)+(0.0472P)²+0.8028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                1207
_reflns_number_total             1690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja502846h_si_002.cif
_cod_data_source_block           n429
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4122308.cif.
;
_cod_original_cell_volume        1911.0(4)
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4122308
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 1.0000 0.40898(10) 0.7500 0.0487(6) Uani 1 2 d S . .
N1 N 1.0000 0.32036(13) 0.7500 0.0342(5) Uani 1 2 d S . .
C1 C 0.91971(14) 0.27063(11) 0.6163(2) 0.0342(5) Uani 1 1 d . . .
C2 C 0.88650(14) 0.29745(11) 0.4641(2) 0.0337(5) Uani 1 1 d . . .
C3 C 0.82233(14) 0.23814(11) 0.3367(2) 0.0360(5) Uani 1 1 d . . .
H3 H 0.8019 0.2542 0.2348 0.043 Uiso 1 1 calc R . .
C4 C 0.78805(14) 0.15399(11) 0.3608(3) 0.0367(5) Uani 1 1 d . . .
C5 C 0.81474(14) 0.12830(11) 0.5077(3) 0.0363(5) Uani 1 1 d . . .
H5 H 0.7875 0.0717 0.5186 0.044 Uiso 1 1 calc R . .
C6 C 0.88044(14) 0.18513(11) 0.6361(2) 0.0342(5) Uani 1 1 d . . .
O2 O 0.92526(10) 0.37980(7) 0.45509(16) 0.0375(4) Uani 1 1 d . . .
C7 C 0.90919(16) 0.40038(11) 0.3091(2) 0.0394(5) Uani 1 1 d . . .
H7A H 0.9378 0.3486 0.2842 0.059 Uiso 1 1 calc R . .
H7B H 0.9450 0.4597 0.3201 0.059 Uiso 1 1 calc R . .
H7C H 0.8339 0.4068 0.2237 0.059 Uiso 1 1 calc R . .
O3 O 0.72520(10) 0.09202(8) 0.24421(17) 0.0422(4) Uani 1 1 d . . .
C8 C 0.69366(17) 0.11163(14) 0.0884(3) 0.0498(6) Uani 1 1 d . . .
H8A H 0.6528 0.1704 0.0490 0.075 Uiso 1 1 calc R . .
H8B H 0.6506 0.0593 0.0175 0.075 Uiso 1 1 calc R . .
H8C H 0.7561 0.1186 0.0923 0.075 Uiso 1 1 calc R . .
O4 O 0.90893(10) 0.17008(7) 0.78258(16) 0.0375(4) Uani 1 1 d . . .
C9 C 0.87554(16) 0.08349(11) 0.8122(3) 0.0410(5) Uani 1 1 d . . .
H9A H 0.7988 0.0794 0.7399 0.062 Uiso 1 1 calc R . .
H9B H 0.8995 0.0831 0.9217 0.062 Uiso 1 1 calc R . .
H9C H 0.9057 0.0291 0.7951 0.062 Uiso 1 1 calc R . .
N2 N 0.0000 0.84206(15) 0.7500 0.0500(7) Uani 1 2 d S . .
O5 O 0.07581(14) 0.79728(11) 0.8643(2) 0.0705(5) Uani 1 1 d . A .
O6 O 0.0225(6) 0.92854(15) 0.7737(18) 0.060(2) Uani 0.50 1 d P A -1
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
O1 N1 C1 120.16(9) . .
O1 N1 C1 120.16(9) . 2_756
C1 N1 C1 119.68(19) . 2_756
N1 C1 C2 120.37(14) . .
N1 C1 C6 119.26(17) . .
C2 C1 C6 119.90(17) . .
O2 C2 C3 123.64(17) . .
O2 C2 C1 116.23(17) . .
C3 C2 C1 120.04(15) . .
C2 C3 C4 118.54(18) . .
C2 C3 H3 120.7 . .
C4 C3 H3 120.7 . .
O3 C4 C5 114.44(15) . .
O3 C4 C3 122.94(18) . .
C5 C4 C3 122.61(18) . .
C6 C5 C4 119.53(16) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
O4 C6 C5 125.23(15) . .
O4 C6 C1 115.49(17) . .
C5 C6 C1 119.20(17) . .
C2 O2 C7 117.47(15) . .
O2 C7 H7A 109.5 . .
O2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
O2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C4 O3 C8 118.81(14) . .
O3 C8 H8A 109.5 . .
O3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 O4 C9 118.33(15) . .
O4 C9 H9A 109.5 . .
O4 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O4 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O5 N2 O5 119.2(2) 2_556 .
O5 N2 O6 132.7(5) 2_556 .
O5 N2 O6 107.8(5) . .
O5 N2 O6 107.8(5) 2_556 2_556
O5 N2 O6 132.8(6) . 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.251(2) .
N1 C1 1.397(2) .
N1 C1 1.397(2) 2_756
C1 C2 1.413(3) .
C1 C6 1.434(2) .
C2 O2 1.3483(19) .
C2 C3 1.380(3) .
C3 C4 1.396(2) .
C3 H3 0.9500 .
C4 O3 1.342(2) .
C4 C5 1.394(3) .
C5 C6 1.368(3) .
C5 H5 0.9500 .
C6 O4 1.348(2) .
O2 C7 1.440(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
O3 C8 1.435(2) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
O4 C9 1.4431(19) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
N2 O5 1.2497(18) 2_556
N2 O5 1.2498(18) .
N2 O6 1.254(4) .
N2 O6 1.254(4) 2_556
