#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/87/1508727.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_1508727
loop_
_publ_author_name
'Samanta, Rajarshi'
'Bauer, Jonathan O.'
'Strohmann, Carsten'
'Antonchick, Andrey P.'
_publ_section_title
;
 Organocatalytic, oxidative, intermolecular amination and hydrazination of
 simple arenes at ambient temperature.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5518
_journal_page_last               5521
_journal_paper_doi               10.1021/ol302607y
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C25 H16 N2 O5'
_chemical_formula_weight         424.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 92.052(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7844(6)
_cell_length_b                   12.8542(5)
_cell_length_c                   11.9648(6)
_cell_measurement_temperature    173(2)
_cell_volume                     1964.95(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16750
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9605
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0354
_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)+(0.0251P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                2734
_reflns_number_total             4282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302607y_si_002.cif
_cod_data_source_block           2064
_cod_database_code               1508727
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.66207(11) 0.04104(10) 0.77698(12) 0.0214(3) Uani 1 1 d .
C2 C 0.56708(11) 0.09851(9) 0.80240(12) 0.0203(3) Uani 1 1 d .
C3 C 0.52983(12) 0.10195(10) 0.91072(12) 0.0249(3) Uani 1 1 d .
H3 H 0.5694 0.0709 0.9706 0.030 Uiso 1 1 calc R
C4 C 0.43640(12) 0.14988(10) 0.93132(12) 0.0280(4) Uani 1 1 d .
H4 H 0.4119 0.1530 1.0053 0.034 Uiso 1 1 calc R
C5 C 0.37798(12) 0.19384(10) 0.84305(12) 0.0277(4) Uani 1 1 d .
H5 H 0.3126 0.2254 0.8572 0.033 Uiso 1 1 calc R
C6 C 0.41295(11) 0.19255(10) 0.73626(12) 0.0240(3) Uani 1 1 d .
H6 H 0.3729 0.2232 0.6765 0.029 Uiso 1 1 calc R
C7 C 0.50839(11) 0.14537(10) 0.71757(12) 0.0205(3) Uani 1 1 d .
C8 C 0.63426(11) 0.10415(10) 0.58494(12) 0.0202(3) Uani 1 1 d .
C9 C 0.68984(10) 0.04626(9) 0.66082(11) 0.0184(3) Uani 1 1 d .
C10 C 0.65767(11) 0.12236(9) 0.46671(12) 0.0215(3) Uani 1 1 d .
C11 C 0.58000(12) 0.10882(9) 0.38487(12) 0.0257(4) Uani 1 1 d .
H11 H 0.5117 0.0886 0.4047 0.031 Uiso 1 1 calc R
C12 C 0.60206(14) 0.12480(10) 0.27400(13) 0.0326(4) Uani 1 1 d .
H12 H 0.5493 0.1129 0.2175 0.039 Uiso 1 1 calc R
C13 C 0.69963(14) 0.15771(11) 0.24483(13) 0.0373(4) Uani 1 1 d .
H13 H 0.7139 0.1695 0.1685 0.045 Uiso 1 1 calc R
C14 C 0.77685(13) 0.17354(11) 0.32647(13) 0.0382(4) Uani 1 1 d .
H14 H 0.8441 0.1970 0.3064 0.046 Uiso 1 1 calc R
C15 C 0.75654(12) 0.15533(11) 0.43778(13) 0.0307(4) Uani 1 1 d .
H15 H 0.8100 0.1653 0.4940 0.037 Uiso 1 1 calc R
C16 C 0.76264(12) -0.08729(10) 0.53767(12) 0.0233(3) Uani 1 1 d .
C17 C 0.86034(12) -0.13767(11) 0.49830(13) 0.0363(4) Uani 1 1 d .
H17A H 0.8841 -0.1904 0.5526 0.054 Uiso 1 1 calc R
H17B H 0.9150 -0.0849 0.4910 0.054 Uiso 1 1 calc R
H17C H 0.8459 -0.1707 0.4255 0.054 Uiso 1 1 calc R
C18 C 0.93422(11) 0.06564(10) 0.70503(12) 0.0222(3) Uani 1 1 d .
C19 C 1.01099(10) 0.03093(10) 0.79206(11) 0.0201(3) Uani 1 1 d .
C20 C 1.09808(11) 0.08092(10) 0.83594(12) 0.0260(4) Uani 1 1 d .
H20 H 1.1181 0.1475 0.8096 0.031 Uiso 1 1 calc R
C21 C 1.15552(11) 0.03070(11) 0.92006(12) 0.0277(4) Uani 1 1 d .
H21 H 1.2156 0.0637 0.9528 0.033 Uiso 1 1 calc R
C22 C 1.12685(11) -0.06688(10) 0.95727(12) 0.0258(4) Uani 1 1 d .
H22 H 1.1671 -0.0993 1.0158 0.031 Uiso 1 1 calc R
C23 C 1.04060(11) -0.11796(10) 0.91069(12) 0.0223(3) Uani 1 1 d .
H23 H 1.0216 -0.1855 0.9349 0.027 Uiso 1 1 calc R
C24 C 0.98356(11) -0.06718(9) 0.82816(12) 0.0199(3) Uani 1 1 d .
C25 C 0.88893(11) -0.10120(10) 0.76390(11) 0.0202(3) Uani 1 1 d .
N1 N 0.77529(9) -0.01425(8) 0.62295(9) 0.0200(3) Uani 1 1 d .
N2 N 0.86572(8) -0.01805(8) 0.68974(9) 0.0206(3) Uani 1 1 d .
O1 O 0.71292(8) -0.00825(7) 0.84835(8) 0.0315(3) Uani 1 1 d .
O2 O 0.54323(7) 0.15049(7) 0.61058(8) 0.0230(2) Uani 1 1 d .
O3 O 0.67697(8) -0.10433(7) 0.49646(8) 0.0300(3) Uani 1 1 d .
O4 O 0.84140(8) -0.18185(7) 0.76498(8) 0.0268(2) Uani 1 1 d .
O5 O 0.92668(8) 0.14726(7) 0.65592(8) 0.0312(3) Uani 1 1 d .
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
O1 C1 C9 123.25(13)
O1 C1 C2 122.53(13)
C9 C1 C2 114.21(12)
C7 C2 C3 118.32(13)
C7 C2 C1 120.10(13)
C3 C2 C1 121.46(13)
C4 C3 C2 120.52(13)
C3 C4 C5 119.50(14)
C6 C5 C4 121.28(14)
C5 C6 C7 118.30(13)
O2 C7 C2 121.43(12)
O2 C7 C6 116.49(12)
C2 C7 C6 122.05(13)
O2 C8 C9 121.65(13)
O2 C8 C10 110.70(11)
C9 C8 C10 127.59(13)
C8 C9 N1 118.38(12)
C8 C9 C1 121.84(13)
N1 C9 C1 119.73(11)
C11 C10 C15 119.98(13)
C11 C10 C8 119.66(13)
C15 C10 C8 120.35(13)
C10 C11 C12 119.75(15)
C13 C12 C11 120.54(15)
C12 C13 C14 119.93(15)
C13 C14 C15 120.12(16)
C14 C15 C10 119.64(15)
O3 C16 N1 120.17(13)
O3 C16 C17 123.28(13)
N1 C16 C17 116.48(13)
O5 C18 N2 124.67(13)
O5 C18 C19 130.37(13)
N2 C18 C19 104.95(11)
C20 C19 C24 121.24(13)
C20 C19 C18 129.68(12)
C24 C19 C18 109.08(12)
C19 C20 C21 117.48(12)
C20 C21 C22 121.10(13)
C23 C22 C21 121.12(13)
C24 C23 C22 117.37(13)
C23 C24 C19 121.66(13)
C23 C24 C25 129.69(12)
C19 C24 C25 108.65(12)
O4 C25 N2 124.34(13)
O4 C25 C24 130.92(12)
N2 C25 C24 104.63(11)
N2 N1 C16 118.21(11)
N2 N1 C9 117.98(10)
C16 N1 C9 122.01(11)
N1 N2 C18 123.81(10)
N1 N2 C25 122.81(11)
C18 N2 C25 112.59(11)
C8 O2 C7 120.08(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2302(15)
C1 C9 1.4483(19)
C1 C2 1.4627(18)
C2 C7 1.3789(18)
C2 C3 1.3973(19)
C3 C4 1.3741(19)
C4 C5 1.3913(19)
C5 C6 1.3688(19)
C6 C7 1.3879(18)
C7 O2 1.3720(16)
C8 O2 1.3522(15)
C8 C9 1.3553(18)
C8 C10 1.4751(19)
C9 N1 1.4279(16)
C10 C11 1.3804(18)
C10 C15 1.3887(19)
C11 C12 1.3813(19)
C12 C13 1.374(2)
C13 C14 1.379(2)
C14 C15 1.386(2)
C16 O3 1.2049(16)
C16 N1 1.3918(17)
C16 C17 1.4978(19)
C18 O5 1.2046(15)
C18 N2 1.3951(16)
C18 C19 1.4743(19)
C19 C20 1.3734(18)
C19 C24 1.3824(17)
C20 C21 1.3843(19)
C21 C22 1.3847(18)
C22 C23 1.3832(18)
C23 C24 1.3716(18)
C24 C25 1.4763(19)
C25 O4 1.2020(14)
C25 N2 1.4137(16)
N1 N2 1.3826(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652050
