#------------------------------------------------------------------------------
#$Date: 2016-03-04 10:32:50 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177338 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/26/1542689.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_1542689
loop_
_publ_author_name
'Pawar, Govind Goroba'
'Brahmanandan, Abhilashamole'
'Kapur, Manmohan'
_publ_section_title
;
 Palladium(II)-Catalyzed, Heteroatom-Directed, Regioselective C-H
 Nitration of Anilines Using Pyrimidine as a Removable Directing Group.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              448
_journal_page_last               451
_journal_paper_doi               10.1021/acs.orglett.5b03493
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C11 H10 N4 O3'
_chemical_formula_weight         246.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4870(12)
_cell_length_b                   13.0919(16)
_cell_length_c                   16.145(2)
_cell_measurement_reflns_used    2830
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.52
_cell_volume                     2216.6(5)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1410
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25090
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.096
_diffrn_reflns_theta_min         2.790
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .09
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1808
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1926
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1502
_reflns_number_total             3258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b03493_si_002.cif
_cod_data_source_block           L3
_cod_original_cell_volume        2216.7(5)
_cod_database_code               1542689
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.66522(15) 0.10183(12) 0.77305(9) 0.0530(5) Uani 1 1 d . .
O2 O 0.73997(16) 0.13175(16) 0.41610(12) 0.0783(7) Uani 1 1 d . .
O3 O 0.87359(15) 0.10895(15) 0.51256(11) 0.0716(6) Uani 1 1 d . .
N1 N 0.38606(18) 0.15132(14) 0.32710(12) 0.0483(5) Uani 1 1 d . .
N2 N 0.49500(16) 0.14068(13) 0.44698(11) 0.0436(5) Uani 1 1 d . .
H6 H 0.5589 0.1492 0.4124 0.052 Uiso 1 1 calc R U
N3 N 0.27094(17) 0.13066(13) 0.45382(12) 0.0421(5) Uani 1 1 d . .
N4 N 0.76422(17) 0.12043(13) 0.48953(13) 0.0444(5) Uani 1 1 d . .
C1 C 0.1604(2) 0.13561(17) 0.32463(16) 0.0508(7) Uani 1 1 d . .
H1 H 0.0832 0.1325 0.2939 0.061 Uiso 1 1 calc R U
C2 C 0.2767(2) 0.14807(18) 0.28675(17) 0.0533(7) Uani 1 1 d . .
H8 H 0.2785 0.1547 0.2282 0.064 Uiso 1 1 calc R U
C3 C 0.3771(2) 0.14048(15) 0.40948(14) 0.0370(5) Uani 1 1 d . .
C4 C 0.5320(2) 0.13004(14) 0.52878(13) 0.0342(5) Uani 1 1 d . .
C5 C 0.44725(19) 0.12898(16) 0.59527(14) 0.0422(6) Uani 1 1 d . .
H5 H 0.3586 0.1355 0.5843 0.051 Uiso 1 1 calc R U
C6 C 0.4867(2) 0.11892(16) 0.67609(14) 0.0428(6) Uani 1 1 d . .
H4 H 0.4253 0.1180 0.7193 0.051 Uiso 1 1 calc R U
C7 C 0.61503(19) 0.11014(15) 0.69513(13) 0.0376(5) Uani 1 1 d . .
C8 C 0.5800(2) 0.1010(2) 0.84080(15) 0.0581(7) Uani 1 1 d . .
H2 H 0.5303 0.1644 0.8410 0.087 Uiso 1 1 calc R U
H10 H 0.6284 0.0956 0.8925 0.087 Uiso 1 1 calc R U
H3 H 0.5222 0.0426 0.8358 0.087 Uiso 1 1 calc R U
C9 C 0.1623(2) 0.12800(17) 0.40930(16) 0.0475(6) Uani 1 1 d . .
H7 H 0.0836 0.1205 0.4378 0.057 Uiso 1 1 calc R U
C10 C 0.66236(18) 0.12019(14) 0.55067(13) 0.0328(5) Uani 1 1 d . .
C11 C 0.70141(19) 0.11073(15) 0.63158(13) 0.0366(5) Uani 1 1 d . .
H9 H 0.7898 0.1045 0.6436 0.044 Uiso 1 1 calc R U
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
C7 O1 C8 117.98(17)
C2 N1 C3 115.2(2)
C3 N2 C4 132.20(19)
C3 N2 H6 113.9
C4 N2 H6 113.9
C3 N3 C9 115.0(2)
O3 N4 O2 120.57(19)
O3 N4 C10 119.03(19)
O2 N4 C10 120.40(17)
C9 C1 C2 116.1(2)
C9 C1 H1 121.9
C2 C1 H1 121.9
N1 C2 C1 123.7(2)
N1 C2 H8 118.1
C1 C2 H8 118.1
N3 C3 N1 127.1(2)
N3 C3 N2 121.0(2)
N1 C3 N2 111.91(19)
N2 C4 C5 123.85(19)
N2 C4 C10 121.18(19)
C5 C4 C10 114.97(19)
C6 C5 C4 122.7(2)
C6 C5 H5 118.7
C4 C5 H5 118.7
C5 C6 C7 120.7(2)
C5 C6 H4 119.6
C7 C6 H4 119.6
O1 C7 C11 115.79(18)
O1 C7 C6 125.8(2)
C11 C7 C6 118.4(2)
O1 C8 H2 109.5
O1 C8 H10 109.5
H2 C8 H10 109.5
O1 C8 H3 109.5
H2 C8 H3 109.5
H10 C8 H3 109.5
N3 C9 C1 122.8(2)
N3 C9 H7 118.6
C1 C9 H7 118.6
C11 C10 C4 122.16(19)
C11 C10 N4 115.24(18)
C4 C10 N4 122.60(19)
C7 C11 C10 121.0(2)
C7 C11 H9 119.5
C10 C11 H9 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.368(3)
O1 C8 1.413(3)
O2 N4 1.222(3)
O3 N4 1.215(2)
N1 C2 1.320(3)
N1 C3 1.341(3)
N2 C3 1.377(3)
N2 C4 1.384(3)
N2 H6 0.8800
N3 C3 1.330(3)
N3 C9 1.348(3)
N4 C10 1.454(3)
C1 C9 1.371(3)
C1 C2 1.374(4)
C1 H1 0.9500
C2 H8 0.9500
C4 C5 1.394(3)
C4 C10 1.418(3)
C5 C6 1.375(3)
C5 H5 0.9500
C6 C7 1.385(3)
C6 H4 0.9500
C7 C11 1.369(3)
C8 H2 0.9800
C8 H10 0.9800
C8 H3 0.9800
C9 H7 0.9500
C10 C11 1.375(3)
C11 H9 0.9500
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
N2 H6 O2 0.88 1.91 2.620(2) 136.1 .
C2 H8 O2 0.95 2.38 3.304(3) 163.4 8_556
C5 H5 N3 0.95 2.30 2.938(3) 124.0 .
C9 H7 O3 0.95 2.52 3.465(3) 177.5 1_455
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
C3 N1 C2 C1 0.6(3)
C9 C1 C2 N1 1.0(3)
C9 N3 C3 N1 2.5(3)
C9 N3 C3 N2 -177.73(19)
C2 N1 C3 N3 -2.5(3)
C2 N1 C3 N2 177.64(19)
C4 N2 C3 N3 1.5(3)
C4 N2 C3 N1 -178.69(19)
C3 N2 C4 C5 -8.6(3)
C3 N2 C4 C10 172.0(2)
N2 C4 C5 C6 -179.59(19)
C10 C4 C5 C6 -0.1(3)
C4 C5 C6 C7 0.6(3)
C8 O1 C7 C11 179.90(18)
C8 O1 C7 C6 0.6(3)
C5 C6 C7 O1 178.63(19)
C5 C6 C7 C11 -0.6(3)
C3 N3 C9 C1 -0.5(3)
C2 C1 C9 N3 -1.1(3)
N2 C4 C10 C11 179.23(18)
C5 C4 C10 C11 -0.2(3)
N2 C4 C10 N4 -0.1(3)
C5 C4 C10 N4 -179.57(18)
O3 N4 C10 C11 2.5(3)
O2 N4 C10 C11 -177.6(2)
O3 N4 C10 C4 -178.08(19)
O2 N4 C10 C4 1.7(3)
O1 C7 C11 C10 -179.07(17)
C6 C7 C11 C10 0.3(3)
C4 C10 C11 C7 0.2(3)
N4 C10 C11 C7 179.56(18)
