#------------------------------------------------------------------------------
#$Date: 2019-11-24 22:41:16 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/69/4516923.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_4516923
loop_
_publ_author_name
'Bag, Raghunath'
'Sar, Dinabandhu'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Aerobic Metal-Free Dioxygenation of Alkenes with tert-Butyl
 Nitrite and N-Hydroxylamines.
;
_journal_issue                   9
_journal_name_full               'ACS omega'
_journal_page_first              6278
_journal_page_last               6290
_journal_paper_doi               10.1021/acsomega.7b01111
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C17 H12 N2 O6'
_chemical_formula_sum            'C17 H12 N2 O6'
_chemical_formula_weight         340.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.798(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3090(9)
_cell_length_b                   5.7406(6)
_cell_length_c                   19.1631(9)
_cell_measurement_reflns_used    1660
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.0390
_cell_measurement_theta_min      3.7210
_cell_volume                     1555.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5243
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0566
_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)+(0.0100P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                1954
_reflns_number_total             2802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b01111_si_001.cif
_cod_data_source_block           rnb_298_j1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4516923
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O4 O 0.12988(12) 0.6444(4) 0.30849(9) 0.0562(5) Uani 1 1 d .
O3 O 0.10978(12) 0.8619(4) 0.48602(9) 0.0591(6) Uani 1 1 d .
O1 O 0.22273(18) 1.2363(4) 0.44857(12) 0.0811(7) Uani 1 1 d .
O2 O 0.22917(15) 0.5744(4) 0.58206(11) 0.0713(7) Uani 1 1 d .
N1 N 0.20589(15) 0.8898(5) 0.50685(11) 0.0529(6) Uani 1 1 d .
O6 O 0.27915(14) 0.6577(5) 0.36416(14) 0.0842(8) Uani 1 1 d .
O5 O 0.2360(2) 0.4052(6) 0.28168(15) 0.1096(10) Uani 1 1 d .
C16 C 0.01537(18) 0.9254(5) 0.32828(13) 0.0456(7) Uani 1 1 d .
N2 N 0.22383(19) 0.5642(6) 0.31983(16) 0.0704(8) Uani 1 1 d .
C11 C -0.05538(18) 0.8252(5) 0.35936(13) 0.0464(7) Uani 1 1 d .
C17 C 0.10952(17) 0.8234(5) 0.35892(13) 0.0464(7) Uani 1 1 d .
H17 H 0.1594 0.9414 0.3677 0.056 Uiso 1 1 calc R
C8 C 0.2575(2) 0.7506(6) 0.55870(14) 0.0514(7) Uani 1 1 d .
C7 C 0.34997(18) 0.8724(6) 0.57509(13) 0.0495(7) Uani 1 1 d .
C1 C 0.2533(2) 1.0917(6) 0.49057(15) 0.0530(7) Uani 1 1 d .
C2 C 0.34797(19) 1.0728(6) 0.53549(14) 0.0520(7) Uani 1 1 d .
C9 C 0.09069(18) 0.7034(6) 0.42655(13) 0.0499(7) Uani 1 1 d .
H9 H 0.1270 0.5587 0.4352 0.060 Uiso 1 1 calc R
C12 C -0.14904(18) 0.8883(6) 0.33722(14) 0.0531(8) Uani 1 1 d .
H12 H -0.1977 0.8180 0.3566 0.064 Uiso 1 1 calc R
C15 C -0.0032(2) 1.0957(6) 0.27693(15) 0.0591(8) Uani 1 1 d .
H15 H 0.0454 1.1634 0.2568 0.071 Uiso 1 1 calc R
C3 C 0.4233(2) 1.2209(7) 0.54057(17) 0.0701(10) Uani 1 1 d .
H3 H 0.4210 1.3561 0.5136 0.084 Uiso 1 1 calc R
C10 C -0.01626(17) 0.6572(6) 0.41641(14) 0.0546(8) Uani 1 1 d .
H10A H -0.0304 0.4976 0.4018 0.066 Uiso 1 1 calc R
H10B H -0.0418 0.6874 0.4596 0.066 Uiso 1 1 calc R
C6 C 0.4297(2) 0.8117(7) 0.62221(15) 0.0671(9) Uani 1 1 d .
H6 H 0.4317 0.6770 0.6494 0.081 Uiso 1 1 calc R
C13 C -0.1680(2) 1.0568(6) 0.28615(15) 0.0650(9) Uani 1 1 d .
H13 H -0.2304 1.1012 0.2711 0.078 Uiso 1 1 calc R
C14 C -0.0964(2) 1.1619(7) 0.25652(16) 0.0680(9) Uani 1 1 d .
H14 H -0.1109 1.2778 0.2227 0.082 Uiso 1 1 calc R
C4 C 0.5029(2) 1.1625(8) 0.5871(2) 0.0819(12) Uani 1 1 d .
H4 H 0.5551 1.2608 0.5916 0.098 Uiso 1 1 calc R
C5 C 0.5073(2) 0.9635(8) 0.62687(19) 0.0814(12) Uani 1 1 d .
H5 H 0.5625 0.9285 0.6574 0.098 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
N2 O4 C17 114.1(2)
N1 O3 C9 111.04(19)
O3 N1 C8 122.3(2)
O3 N1 C1 121.7(2)
C8 N1 C1 114.2(2)
C11 C16 C15 122.0(3)
C11 C16 C17 110.1(2)
C15 C16 C17 128.0(3)
O6 N2 O5 129.3(3)
O6 N2 O4 118.4(3)
O5 N2 O4 112.3(3)
C16 C11 C12 119.8(3)
C16 C11 C10 111.5(2)
C12 C11 C10 128.6(3)
O4 C17 C16 105.73(19)
O4 C17 C9 108.7(2)
C16 C17 C9 104.1(2)
O2 C8 N1 125.2(3)
O2 C8 C7 131.1(3)
N1 C8 C7 103.8(3)
C2 C7 C6 121.0(3)
C2 C7 C8 109.5(2)
C6 C7 C8 129.5(3)
O1 C1 N1 125.9(3)
O1 C1 C2 130.3(3)
N1 C1 C2 103.8(2)
C3 C2 C7 122.1(3)
C3 C2 C1 129.3(3)
C7 C2 C1 108.6(3)
O3 C9 C17 110.3(2)
O3 C9 C10 105.8(2)
C17 C9 C10 105.8(2)
C13 C12 C11 118.5(3)
C16 C15 C14 117.8(3)
C2 C3 C4 117.4(4)
C11 C10 C9 103.6(2)
C7 C6 C5 116.7(3)
C12 C13 C14 121.4(3)
C13 C14 C15 120.4(3)
C5 C4 C3 121.8(4)
C4 C5 C6 120.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 N2 1.406(3)
O4 C17 1.470(3)
O3 N1 1.381(3)
O3 C9 1.452(3)
O1 C1 1.192(3)
O2 C8 1.201(4)
N1 C8 1.395(3)
N1 C1 1.402(4)
O6 N2 1.196(3)
O5 N2 1.199(4)
C16 C11 1.376(4)
C16 C15 1.384(4)
C16 C17 1.503(3)
C11 C12 1.390(3)
C11 C10 1.501(4)
C17 C9 1.528(4)
C8 C7 1.487(4)
C7 C2 1.376(4)
C7 C6 1.387(4)
C1 C2 1.494(4)
C2 C3 1.365(4)
C9 C10 1.536(3)
C12 C13 1.373(4)
C15 C14 1.384(4)
C3 C4 1.375(5)
C6 C5 1.403(5)
C13 C14 1.384(4)
C4 C5 1.370(5)
