#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222728.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222728
loop_
_publ_author_name
'Tang, Shi-Gui'
'Wang, Jian-Qiang'
'Guo, Cheng'
_publ_section_title
;
 tert-Butyl
 N-{4-methyl-3-[4-(3-pyridyl)pyrimidin-2-yloxy]phenyl}carbamate
;
_journal_coeditor_code           HK2725
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1849
_journal_paper_doi               10.1107/S1600536809025604
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H22 N4 O3'
_chemical_formula_moiety         'C21 H22 N4 O3'
_chemical_formula_sum            'C21 H22 N4 O3'
_chemical_formula_weight         378.43
_chemical_name_systematic
;
tert-Butyl N-{4-methyl-3-[4-(3-pyridyl)pyrimidin-2-
yloxy]phenyl}carbamate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.74(3)
_cell_angle_beta                 107.14(3)
_cell_angle_gamma                99.97(3)
_cell_formula_units_Z            2
_cell_length_a                   9.951(2)
_cell_length_b                   10.733(2)
_cell_length_c                   11.577(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1008.6(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3882
_diffrn_reflns_theta_full        25.29
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.273
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0583
_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)+(0.1P)²+0.07P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1836
_reflns_number_gt                2333
_reflns_number_total             3652
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2725.cif
_cod_data_source_block           I
_cod_database_code               2222728
_cod_database_fobs_code          2222728
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0153(2) 0.8866(2) 0.2102(2) 0.0600(6) Uani d . 1 . .
O O2 0.0613(2) 0.7528(2) 0.3167(2) 0.0719(7) Uani d . 1 . .
O O3 0.4840(2) 0.8449(2) 0.7311(2) 0.0594(6) Uani d . 1 . .
N N1 0.2087(2) 0.9880(2) 0.4085(2) 0.0498(6) Uani d . 1 . .
H H1A 0.2141 1.0599 0.3929 0.060 Uiso calc R 1 . .
N N2 0.2426(2) 0.7463(2) 0.7031(2) 0.0429(5) Uani d . 1 . .
N N3 0.4351(3) 0.6437(3) 0.7463(3) 0.0574(7) Uani d . 1 . .
N N4 -0.1874(3) 0.7568(2) 0.6228(3) 0.0567(7) Uani d . 1 . .
C C1 -0.1644(4) 0.8538(4) 0.0096(4) 0.0910(12) Uani d . 1 . .
H H1B -0.1731 0.9458 0.0640 0.136 Uiso calc R 1 . .
H H1C -0.2570 0.7920 -0.0708 0.136 Uiso calc R 1 . .
H H1D -0.0855 0.8694 -0.0200 0.136 Uiso calc R 1 . .
C C2 -0.1138(4) 0.6358(4) 0.0150(4) 0.0862(11) Uani d . 1 . .
H H2B -0.0922 0.5919 0.0724 0.129 Uiso calc R 1 . .
H H2C -0.0339 0.6503 -0.0136 0.129 Uiso calc R 1 . .
H H2D -0.2057 0.5727 -0.0659 0.129 Uiso calc R 1 . .
C C3 -0.2421(4) 0.7685(5) 0.1575(4) 0.0929(12) Uani d . 1 . .
H H3B -0.2485 0.8630 0.2080 0.139 Uiso calc R 1 . .
H H3C -0.2119 0.7312 0.2196 0.139 Uiso calc R 1 . .
H H3D -0.3381 0.7032 0.0834 0.139 Uiso calc R 1 . .
C C4 -0.1288(3) 0.7813(3) 0.0971(3) 0.0550(8) Uani d . 1 . .
C C5 0.0919(3) 0.8649(3) 0.3128(3) 0.0490(7) Uani d . 1 . .
C C6 0.3229(3) 1.0147(3) 0.5304(3) 0.0417(6) Uani d . 1 . .
C C7 0.4275(3) 1.1551(3) 0.6155(3) 0.0515(7) Uani d . 1 . .
H H7A 0.4202 1.2258 0.5898 0.062 Uiso calc R 1 . .
C C8 0.5415(3) 1.1899(3) 0.7372(3) 0.0573(8) Uani d . 1 . .
H H8A 0.6102 1.2844 0.7926 0.069 Uiso calc R 1 . .
C C9 0.5577(3) 1.0880(3) 0.7807(3) 0.0505(7) Uani d . 1 . .
C C10 0.4535(3) 0.9502(3) 0.6937(3) 0.0449(6) Uani d . 1 . .
C C11 0.3367(3) 0.9096(3) 0.5703(3) 0.0459(7) Uani d . 1 . .
H H11A 0.2689 0.8147 0.5150 0.055 Uiso calc R 1 . .
C C12 0.6828(4) 1.1258(4) 0.9146(3) 0.0766(10) Uani d . 1 . .
H H12A 0.6742 1.0413 0.9256 0.115 Uiso calc R 1 . .
H H12B 0.6764 1.2028 0.9920 0.115 Uiso calc R 1 . .
H H12C 0.7773 1.1573 0.9114 0.115 Uiso calc R 1 . .
C C13 0.3789(3) 0.7420(3) 0.7256(3) 0.0446(6) Uani d . 1 . .
C C14 0.3369(3) 0.5396(3) 0.7410(3) 0.0610(8) Uani d . 1 . .
H H14A 0.3692 0.4692 0.7562 0.073 Uiso calc R 1 . .
C C15 0.1907(3) 0.5281(3) 0.7147(3) 0.0569(8) Uani d . 1 . .
H H15A 0.1244 0.4510 0.7090 0.068 Uiso calc R 1 . .
C C16 0.1453(3) 0.6373(3) 0.6967(2) 0.0404(6) Uani d . 1 . .
C C17 -0.0094(3) 0.6389(3) 0.6684(3) 0.0404(6) Uani d . 1 . .
C C18 -0.1188(3) 0.5330(3) 0.6602(3) 0.0507(7) Uani d . 1 . .
H H18A -0.0970 0.4574 0.6725 0.061 Uiso calc R 1 . .
C C19 -0.2597(3) 0.5405(3) 0.6339(3) 0.0571(8) Uani d . 1 . .
H H19A -0.3347 0.4697 0.6277 0.068 Uiso calc R 1 . .
C C20 -0.2896(3) 0.6538(3) 0.6167(3) 0.0525(7) Uani d . 1 . .
H H20A -0.3854 0.6584 0.6000 0.063 Uiso calc R 1 . .
C C21 -0.0505(3) 0.7479(3) 0.6477(3) 0.0519(7) Uani d . 1 . .
H H21A 0.0217 0.8189 0.6514 0.062 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C4 . . 122.7(2) ?
C13 O3 C10 . . 123.90(19) ?
C5 N1 C6 . . 128.6(2) ?
C5 N1 H1A . . 115.7 ?
C6 N1 H1A . . 115.7 ?
C13 N2 C16 . . 116.2(2) ?
C14 N3 C13 . . 113.6(2) ?
C4 C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C4 C2 H2B . . 109.5 ?
C4 C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C2 H2D . . 109.5 ?
H2B C2 H2D . . 109.5 ?
H2C C2 H2D . . 109.5 ?
C4 C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C4 C3 H3D . . 109.5 ?
H3B C3 H3D . . 109.5 ?
H3C C3 H3D . . 109.5 ?
C20 N4 C21 . . 117.2(2) ?
O1 C4 C3 . . 109.0(3) ?
O1 C4 C2 . . 110.8(2) ?
C3 C4 C2 . . 112.3(3) ?
O1 C4 C1 . . 102.0(2) ?
C3 C4 C1 . . 111.1(3) ?
C2 C4 C1 . . 111.1(3) ?
O2 C5 O1 . . 125.6(3) ?
O2 C5 N1 . . 126.3(3) ?
O1 C5 N1 . . 108.1(2) ?
C7 C6 C11 . . 118.9(2) ?
C7 C6 N1 . . 117.0(2) ?
C11 C6 N1 . . 124.0(2) ?
C8 C7 C6 . . 120.3(3) ?
C8 C7 H7A . . 119.8 ?
C6 C7 H7A . . 119.8 ?
C7 C8 C9 . . 122.2(3) ?
C7 C8 H8A . . 118.9 ?
C9 C8 H8A . . 118.9 ?
C10 C9 C8 . . 116.0(3) ?
C10 C9 C12 . . 121.7(3) ?
C8 C9 C12 . . 122.3(3) ?
C9 C10 C11 . . 124.2(2) ?
C9 C10 O3 . . 114.6(2) ?
C11 C10 O3 . . 120.9(2) ?
C10 C11 C6 . . 118.4(2) ?
C10 C11 H11A . . 120.8 ?
C6 C11 H11A . . 120.8 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N2 C13 O3 . . 120.7(2) ?
N2 C13 N3 . . 128.4(3) ?
O3 C13 N3 . . 110.9(2) ?
N3 C14 C15 . . 124.3(3) ?
N3 C14 H14A . . 117.8 ?
C15 C14 H14A . . 117.8 ?
C14 C15 C16 . . 117.1(3) ?
C14 C15 H15A . . 121.4 ?
C16 C15 H15A . . 121.4 ?
N2 C16 C15 . . 120.4(2) ?
N2 C16 C17 . . 116.8(2) ?
C15 C16 C17 . . 122.8(2) ?
C18 C17 C21 . . 117.2(2) ?
C18 C17 C16 . . 122.0(2) ?
C21 C17 C16 . . 120.8(2) ?
C19 C18 C17 . . 119.3(2) ?
C19 C18 H18A . . 120.3 ?
C17 C18 H18A . . 120.3 ?
C18 C19 C20 . . 119.4(3) ?
C18 C19 H19A . . 120.3 ?
C20 C19 H19A . . 120.3 ?
N4 C20 C19 . . 122.8(3) ?
N4 C20 H20A . . 118.6 ?
C19 C20 H20A . . 118.6 ?
N4 C21 C17 . . 124.0(2) ?
N4 C21 H21A . . 118.0 ?
C17 C21 H21A . . 118.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.463(3) ?
O1 C5 . 1.344(3) ?
O2 C5 . 1.211(3) ?
O3 C10 . 1.418(3) ?
O3 C13 . 1.349(3) ?
N1 C5 . 1.345(3) ?
N1 C6 . 1.403(3) ?
N1 H1A . 0.8600 ?
N3 C13 . 1.349(3) ?
N3 C14 . 1.318(4) ?
N4 C20 . 1.327(3) ?
N4 C21 . 1.336(3) ?
C1 C4 . 1.518(4) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
N2 C13 . 1.317(3) ?
N2 C16 . 1.344(3) ?
C2 C4 . 1.512(4) ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C2 H2D . 0.9600 ?
C3 C4 . 1.507(5) ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C3 H3D . 0.9600 ?
C6 C7 . 1.391(4) ?
C6 C11 . 1.399(3) ?
C7 C8 . 1.373(4) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.396(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.372(4) ?
C9 C12 . 1.509(4) ?
C10 C11 . 1.380(4) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C14 C15 . 1.367(4) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.397(3) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.482(4) ?
C17 C18 . 1.380(4) ?
C17 C21 . 1.391(3) ?
C18 C19 . 1.368(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.379(4) ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9300 ?
C21 H21A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A N4 2_576 0.86 2.10 2.944(4) 165
C15 H15A O2 2_566 0.93 2.45 3.382(4) 177
C18 H18A O2 2_566 0.93 2.39 3.319(4) 174
C3 H3B Cg1 2_576 0.96 2.86 3.560(3) 131
C12 H12B Cg2 2_677 0.96 2.90 3.788(3) 154
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 C4 C3 . . . . 64.0(3) ?
C5 O1 C4 C2 . . . . -60.1(4) ?
C5 O1 C4 C1 . . . . -178.5(3) ?
C4 O1 C5 O2 . . . . 8.5(5) ?
C4 O1 C5 N1 . . . . -172.4(2) ?
C6 N1 C5 O2 . . . . 2.1(5) ?
C6 N1 C5 O1 . . . . -177.0(2) ?
C5 N1 C6 C7 . . . . -177.0(3) ?
C5 N1 C6 C11 . . . . 2.9(4) ?
C11 C6 C7 C8 . . . . -0.6(4) ?
N1 C6 C7 C8 . . . . 179.3(3) ?
C6 C7 C8 C9 . . . . 0.0(5) ?
C7 C8 C9 C10 . . . . 0.6(4) ?
C7 C8 C9 C12 . . . . -179.9(3) ?
C8 C9 C10 C11 . . . . -0.7(4) ?
C12 C9 C10 C11 . . . . 179.9(3) ?
C8 C9 C10 O3 . . . . 172.1(2) ?
C12 C9 C10 O3 . . . . -7.3(4) ?
C13 O3 C10 C9 . . . . 138.8(3) ?
C13 O3 C10 C11 . . . . -48.2(4) ?
C9 C10 C11 C6 . . . . 0.1(4) ?
O3 C10 C11 C6 . . . . -172.3(2) ?
C7 C6 C11 C10 . . . . 0.6(4) ?
N1 C6 C11 C10 . . . . -179.3(2) ?
C16 N2 C13 O3 . . . . 178.7(2) ?
C16 N2 C13 N3 . . . . -1.6(4) ?
C10 O3 C13 N2 . . . . -9.7(4) ?
C10 O3 C13 N3 . . . . 170.6(2) ?
C14 N3 C13 N2 . . . . 0.8(4) ?
C14 N3 C13 O3 . . . . -179.5(2) ?
C13 N3 C14 C15 . . . . 1.1(5) ?
N3 C14 C15 C16 . . . . -2.0(5) ?
C13 N2 C16 C15 . . . . 0.5(4) ?
C13 N2 C16 C17 . . . . -178.7(2) ?
C14 C15 C16 N2 . . . . 1.1(4) ?
C14 C15 C16 C17 . . . . -179.7(3) ?
N2 C16 C17 C18 . . . . -179.7(2) ?
C15 C16 C17 C18 . . . . 1.1(4) ?
N2 C16 C17 C21 . . . . 0.9(4) ?
C15 C16 C17 C21 . . . . -178.3(3) ?
C21 C17 C18 C19 . . . . -0.6(4) ?
C16 C17 C18 C19 . . . . 180.0(2) ?
C17 C18 C19 C20 . . . . -0.3(4) ?
C21 N4 C20 C19 . . . . -0.4(4) ?
C18 C19 C20 N4 . . . . 0.8(5) ?
C20 N4 C21 C17 . . . . -0.6(4) ?
C18 C17 C21 N4 . . . . 1.1(4) ?
C16 C17 C21 N4 . . . . -179.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742758
