#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025546.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_4025546
loop_
_publ_author_name
'Alexander O. Terent'ev'
'Dmitry A. Borisov'
'Ivan A. Yaremenko'
'Vladimir V. Chernyshev'
'Gennady I. Nikishin'
_publ_contact_author             V.V.Chernyshev
_publ_contact_author_address
;
      Department of Chemistry 
      Moscow State University
      119991 Moscow
      Russia
;
_publ_contact_author_email       vladimir@struct.chem.msu.ru
_publ_contact_author_fax         '+ 7-495-9390898'
_publ_contact_author_name        'Dr. Vladimir V. Chernyshev'
_publ_contact_author_phone       '+ 7-495-9393654'
_publ_section_title
;
 Synthesis of Asymmetric Peroxides: Transition Metal (Cu, Fe, Mn, Co)
 Catalyzed Peroxidation of β-Dicarbonyl Compounds with tert-Butyl
 Hydroperoxide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5065
_journal_page_last               5071
_journal_paper_doi               10.1021/jo100793j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C16 H21 N O6'
_chemical_formula_sum            'C16 H21 N O6'
_chemical_formula_weight         323.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   7.2714(16)
_cell_length_b                   18.978(3)
_cell_length_c                   25.506(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.48
_cell_measurement_theta_min      27.33
_cell_volume                     3519.7(10)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3324
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1028P)²+1.4526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2160
_reflns_number_gt                2258
_reflns_number_total             3324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100793j_si_003.cif
_cod_data_source_block           ioh28
_cod_original_cell_volume        3519.8(10)
_cod_database_code               4025546
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 0.2173(3) 0.85619(9) 0.10464(7) 0.0523(5) Uani 1 1 d . . .
O2 O 0.2760(3) 0.78215(9) 0.10129(7) 0.0619(6) Uani 1 1 d . . .
C3 C 0.2844(4) 0.88830(12) 0.05827(9) 0.0466(6) Uani 1 1 d . . .
C4 C 0.2005(4) 0.96300(14) 0.05751(11) 0.0511(6) Uani 1 1 d . . .
O5 O 0.2298(4) 0.99910(11) 0.01942(9) 0.0729(7) Uani 1 1 d . . .
C6 C 0.5709(4) 0.93503(14) 0.10293(11) 0.0521(7) Uani 1 1 d . . .
C7 C 0.4955(4) 0.89345(14) 0.05772(11) 0.0546(7) Uani 1 1 d . . .
H7A H 0.5469 0.8463 0.0587 0.065 Uiso 1 1 calc . . .
H7B H 0.5343 0.9154 0.0252 0.065 Uiso 1 1 calc . . .
O8 O 0.3110(4) 0.83898(13) -0.02730(9) 0.0898(8) Uani 1 1 d . . .
C9 C 0.5969(4) 1.00738(15) 0.09919(11) 0.0568(7) Uani 1 1 d . . .
H9 H 0.5689 1.0302 0.0679 0.068 Uiso 1 1 calc . . .
C10 C 0.2118(5) 0.84965(14) 0.00906(11) 0.0603(8) Uani 1 1 d . . .
C11 C 0.6809(5) 0.9410(2) 0.19210(13) 0.0796(11) Uani 1 1 d . . .
H11 H 0.7093 0.9191 0.2237 0.096 Uiso 1 1 calc . . .
C12 C 0.6153(5) 0.90240(17) 0.14991(13) 0.0676(9) Uani 1 1 d . . .
H12 H 0.6009 0.8539 0.1532 0.081 Uiso 1 1 calc . . .
C13 C 0.6633(4) 1.04585(17) 0.14061(13) 0.0632(8) Uani 1 1 d . . .
H13 H 0.6808 1.0942 0.1374 0.076 Uiso 1 1 calc . . .
C14 C 0.2017(5) 0.74500(16) 0.14605(12) 0.0707(9) Uani 1 1 d . . .
C15 C 0.7029(4) 1.0125(2) 0.18623(12) 0.0677(9) Uani 1 1 d . . .
N16 N 0.7733(5) 1.0538(3) 0.23091(14) 0.0956(11) Uani 1 1 d . . .
O17 O 0.7810(6) 1.0245(3) 0.27340(13) 0.1460(16) Uani 1 1 d . . .
C18 C 0.0924(5) 0.98733(17) 0.10280(14) 0.0759(10) Uani 1 1 d . . .
H18A H 0.0466 1.0339 0.0961 0.114 Uiso 1 1 calc R . .
H18B H 0.1690 0.9881 0.1334 0.114 Uiso 1 1 calc R . .
H18C H -0.0091 0.9559 0.1085 0.114 Uiso 1 1 calc R . .
C19 C 0.0120(5) 0.8314(2) 0.00880(14) 0.0861(12) Uani 1 1 d . . .
H19A H -0.0573 0.8704 -0.0047 0.129 Uiso 1 1 calc R . .
H19B H -0.0275 0.8212 0.0439 0.129 Uiso 1 1 calc R . .
H19C H -0.0075 0.7907 -0.0129 0.129 Uiso 1 1 calc R . .
O20 O 0.8162(6) 1.1151(2) 0.22293(15) 0.1412(15) Uani 1 1 d . . .
C21 C -0.0078(6) 0.7487(2) 0.14535(16) 0.0956(13) Uani 1 1 d . . .
H21A H -0.0462 0.7967 0.1497 0.143 Uiso 1 1 calc R . .
H21B H -0.0564 0.7207 0.1735 0.143 Uiso 1 1 calc R . .
H21C H -0.0526 0.7310 0.1125 0.143 Uiso 1 1 calc R . .
C22 C 0.2770(8) 0.7737(3) 0.19651(14) 0.1181(19) Uani 1 1 d . . .
H22A H 0.4071 0.7654 0.1980 0.177 Uiso 1 1 calc R . .
H22B H 0.2183 0.7506 0.2255 0.177 Uiso 1 1 calc R . .
H22C H 0.2537 0.8234 0.1983 0.177 Uiso 1 1 calc R . .
C23 C 0.2617(7) 0.67014(19) 0.13419(18) 0.1098(16) Uani 1 1 d . . .
H23A H 0.2167 0.6566 0.1003 0.165 Uiso 1 1 calc R . .
H23B H 0.2127 0.6389 0.1603 0.165 Uiso 1 1 calc R . .
H23C H 0.3935 0.6676 0.1345 0.165 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 O1 O2 105.21(16) . . ?
C14 O2 O1 108.1(2) . . ?
O1 C3 C7 112.2(2) . . ?
O1 C3 C4 105.6(2) . . ?
C7 C3 C4 109.6(2) . . ?
O1 C3 C10 110.8(2) . . ?
C7 C3 C10 111.3(2) . . ?
C4 C3 C10 106.9(2) . . ?
O5 C4 C18 123.2(3) . . ?
O5 C4 C3 117.5(2) . . ?
C18 C4 C3 119.3(2) . . ?
C12 C6 C9 117.9(3) . . ?
C12 C6 C7 120.9(3) . . ?
C9 C6 C7 121.1(3) . . ?
C6 C7 C3 113.0(2) . . ?
C6 C7 H7A 109.0 . . ?
C3 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C3 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C13 C9 C6 121.4(3) . . ?
C13 C9 H9 119.3 . . ?
C6 C9 H9 119.3 . . ?
O8 C10 C19 123.1(3) . . ?
O8 C10 C3 120.4(3) . . ?
C19 C10 C3 116.5(3) . . ?
C15 C11 C12 118.5(3) . . ?
C15 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C6 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C6 C12 H12 119.5 . . ?
C15 C13 C9 119.2(3) . . ?
C15 C13 H13 120.4 . . ?
C9 C13 H13 120.4 . . ?
O2 C14 C22 111.3(3) . . ?
O2 C14 C23 101.1(3) . . ?
C22 C14 C23 114.0(4) . . ?
O2 C14 C21 110.0(3) . . ?
C22 C14 C21 111.0(4) . . ?
C23 C14 C21 109.2(3) . . ?
C13 C15 C11 122.0(3) . . ?
C13 C15 N16 119.3(4) . . ?
C11 C15 N16 118.7(3) . . ?
O17 N16 O20 124.8(4) . . ?
O17 N16 C15 117.4(4) . . ?
O20 N16 C15 117.8(4) . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C3 1.417(3) . ?
O1 O2 1.471(2) . ?
O2 C14 1.447(3) . ?
C3 C7 1.538(4) . ?
C3 C4 1.544(3) . ?
C3 C10 1.547(4) . ?
C4 O5 1.208(3) . ?
C4 C18 1.472(4) . ?
C6 C12 1.387(4) . ?
C6 C9 1.389(4) . ?
C6 C7 1.501(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O8 C10 1.192(4) . ?
C9 C13 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C19 1.494(5) . ?
C11 C15 1.373(5) . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C15 1.356(4) . ?
C13 H13 0.9300 . ?
C14 C22 1.501(5) . ?
C14 C23 1.517(5) . ?
C14 C21 1.525(5) . ?
C15 N16 1.475(5) . ?
N16 O17 1.219(5) . ?
N16 O20 1.221(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B O5 0.97 2.62 3.467(6) 146 5_675
C18 H18B O17 0.97 2.61 3.514(6) 158 6_556
