#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223108.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_2223108
loop_
_publ_author_name
'Sheng, Chao'
'Xu, Qing-Bing'
'Liu, Yuan-Yuan'
'Zhu, Hong-Jun'
_publ_section_title
;
 Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate
;
_journal_coeditor_code           HK2749
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2117
_journal_paper_doi               10.1107/S1600536809030736
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H17 Cl N2 O5'
_chemical_formula_moiety         'C16 H17 Cl N2 O5'
_chemical_formula_sum            'C16 H17 Cl N2 O5'
_chemical_formula_weight         352.77
_chemical_name_systematic
;
Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate
;
_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                101.24(3)
_cell_angle_beta                 108.47(3)
_cell_angle_gamma                113.42(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5030(19)
_cell_length_b                   10.051(2)
_cell_length_c                   11.162(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     862.6(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3346
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.453
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3140
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0776
_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                1427
_reflns_number_total             3140
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2749.cif
_cod_data_source_block           I
_cod_database_code               2223108
_cod_database_fobs_code          2223108
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
Cl Cl 0.16863(16) 0.54848(17) 0.23573(15) 0.0918(5) Uani d . 1 . .
O O1 -0.7131(4) 0.4178(4) -0.3468(3) 0.0806(10) Uani d . 1 . .
O O2 -0.6406(5) 0.2829(5) -0.4869(4) 0.1119(14) Uani d . 1 . .
O O3 -0.5192(5) 0.0798(5) -0.3027(4) 0.1150(14) Uani d . 1 . .
O O4 -0.7857(7) -0.0410(6) -0.4408(5) 0.1371(18) Uani d U 1 . .
O O5 -0.4458(3) 0.3794(3) -0.0203(3) 0.0658(9) Uani d . 1 . .
N N1 -0.3799(5) 0.1982(4) 0.0434(4) 0.0631(11) Uani d . 1 . .
N N2 -0.0880(5) 0.2702(5) 0.1614(4) 0.0727(11) Uani d . 1 . .
C C1 -0.8435(9) 0.4438(9) -0.4217(6) 0.131(3) Uani d . 1 . .
H H1B -0.8231 0.5446 -0.3730 0.196 Uiso calc R 1 . .
H H1C -0.9517 0.3648 -0.4345 0.196 Uiso calc R 1 . .
H H1D -0.8443 0.4398 -0.5086 0.196 Uiso calc R 1 . .
C C2 -0.6907(10) 0.2967(8) -0.6060(6) 0.140(3) Uani d . 1 . .
H H2B -0.6124 0.2972 -0.6432 0.210 Uiso calc R 1 . .
H H2C -0.6938 0.3925 -0.5950 0.210 Uiso calc R 1 . .
H H2D -0.8026 0.2105 -0.6664 0.210 Uiso calc R 1 . .
C C3 -0.7194(7) 0.2788(5) -0.4025(5) 0.0710(14) Uani d . 1 . .
H H3A -0.8400 0.2004 -0.4578 0.085 Uiso calc R 1 . .
C C4 -0.5126(8) -0.0639(7) -0.3384(6) 0.1142(16) Uani d . 1 . .
H H4A -0.3983 -0.0432 -0.2896 0.171 Uiso calc R 1 . .
H H4B -0.5469 -0.1044 -0.4343 0.171 Uiso calc R 1 . .
H H4C -0.5883 -0.1389 -0.3148 0.171 Uiso calc R 1 . .
C C5 -0.6598(11) 0.0736(9) -0.3573(8) 0.1142(16) Uani d U 1 . .
C C6 -0.6513(6) 0.2253(6) -0.2981(5) 0.0688(13) Uani d U 1 . .
H H6A -0.5298 0.3025 -0.2460 0.083 Uiso calc R 1 . .
C C7 -0.7250(6) 0.2132(5) -0.1948(5) 0.0517(11) Uani d . 1 . .
C C8 -0.6183(5) 0.2823(4) -0.0593(5) 0.0464(10) Uani d . 1 . .
C C9 -0.6753(6) 0.2753(5) 0.0390(5) 0.0609(13) Uani d . 1 . .
H H9A -0.5986 0.3259 0.1305 0.073 Uiso calc R 1 . .
C C10 -0.8481(7) 0.1921(6) 0.0000(6) 0.0699(14) Uani d . 1 . .
H H10A -0.8884 0.1850 0.0656 0.084 Uiso calc R 1 . .
C C11 -0.9602(6) 0.1202(6) -0.1340(7) 0.0793(16) Uani d . 1 . .
H H11A -1.0770 0.0644 -0.1607 0.095 Uiso calc R 1 . .
C C12 -0.8968(6) 0.1316(5) -0.2302(5) 0.0691(14) Uani d . 1 . .
H H12A -0.9732 0.0823 -0.3218 0.083 Uiso calc R 1 . .
C C13 -0.3283(6) 0.3428(5) 0.0417(4) 0.0536(11) Uani d . 1 . .
C C14 -0.2533(6) 0.1731(5) 0.1042(5) 0.0720(14) Uani d . 1 . .
H H14A -0.2858 0.0737 0.1068 0.086 Uiso calc R 1 . .
C C15 -0.0453(6) 0.4133(5) 0.1578(4) 0.0586(12) Uani d . 1 . .
C C16 -0.1620(5) 0.4550(5) 0.0963(4) 0.0575(12) Uani d . 1 . .
H H16A -0.1295 0.5538 0.0923 0.069 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'
Cl Cl 0.1484 0.1585 '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
C3 O1 C1 . . 117.8(4) ?
C2 O2 C3 . . 126.5(5) ?
C5 O3 C4 . . 117.8(5) ?
C13 O5 C8 . . 121.1(3) ?
C14 N1 C13 . . 114.1(4) ?
C14 N2 C15 . . 114.3(4) ?
O1 C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
O2 C2 H2B . . 109.5 ?
O2 C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
O2 C2 H2D . . 109.5 ?
H2B C2 H2D . . 109.5 ?
H2C C2 H2D . . 109.5 ?
O2 C3 O1 . . 114.2(4) ?
O2 C3 C6 . . 109.9(4) ?
O1 C3 C6 . . 111.5(4) ?
O2 C3 H3A . . 107.0 ?
O1 C3 H3A . . 107.0 ?
C6 C3 H3A . . 107.0 ?
O3 C4 H4A . . 109.5 ?
O3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
O3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O4 C5 O3 . . 123.8(7) ?
O4 C5 C6 . . 124.5(7) ?
O3 C5 C6 . . 111.6(7) ?
C3 C6 C5 . . 112.0(5) ?
C3 C6 C7 . . 117.1(4) ?
C5 C6 C7 . . 108.8(4) ?
C3 C6 H6A . . 106.1 ?
C5 C6 H6A . . 106.1 ?
C7 C6 H6A . . 106.1 ?
C8 C7 C12 . . 116.5(4) ?
C8 C7 C6 . . 119.9(4) ?
C12 C7 C6 . . 123.6(4) ?
C7 C8 C9 . . 123.0(4) ?
C7 C8 O5 . . 117.6(4) ?
C9 C8 O5 . . 118.9(4) ?
C8 C9 C10 . . 118.9(4) ?
C8 C9 H9A . . 120.5 ?
C10 C9 H9A . . 120.5 ?
C11 C10 C9 . . 120.4(5) ?
C11 C10 H10A . . 119.8 ?
C9 C10 H10A . . 119.8 ?
C10 C11 C12 . . 118.7(5) ?
C10 C11 H11A . . 120.6 ?
C12 C11 H11A . . 120.6 ?
C7 C12 C11 . . 122.4(5) ?
C7 C12 H12A . . 118.8 ?
C11 C12 H12A . . 118.8 ?
O5 C13 N1 . . 119.0(4) ?
O5 C13 C16 . . 117.2(4) ?
N1 C13 C16 . . 123.9(4) ?
N2 C14 N1 . . 128.5(4) ?
N2 C14 H14A . . 115.7 ?
N1 C14 H14A . . 115.7 ?
N2 C15 C16 . . 123.5(4) ?
N2 C15 Cl . . 116.9(4) ?
C16 C15 Cl . . 119.6(4) ?
C13 C16 C15 . . 115.6(4) ?
C13 C16 H16A . . 122.2 ?
C15 C16 H16A . . 122.2 ?
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
Cl C15 . 1.720(5) ?
O1 C1 . 1.410(6) ?
O1 C3 . 1.383(5) ?
O2 C2 . 1.318(6) ?
O2 C3 . 1.373(5) ?
O3 C4 . 1.453(6) ?
O3 C5 . 1.250(7) ?
O4 C5 . 1.186(8) ?
O5 C8 . 1.393(4) ?
O5 C13 . 1.341(5) ?
N1 C13 . 1.343(5) ?
N1 C14 . 1.327(5) ?
N2 C14 . 1.316(5) ?
N2 C15 . 1.343(5) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C2 H2D . 0.9600 ?
C3 C6 . 1.452(6) ?
C3 H3A . 0.9800 ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.498(8) ?
C6 C7 . 1.528(6) ?
C6 H6A . 0.9800 ?
C7 C8 . 1.363(5) ?
C7 C12 . 1.376(6) ?
C8 C9 . 1.370(6) ?
C9 C10 . 1.378(6) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.361(7) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.390(7) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 C16 . 1.359(5) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.370(5) ?
C16 H16A . 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
_geom_hbond_publ_flag
C6 H6A O5 . 0.98 2.25 2.777(6) 113 yes
C1 H1B Cg2 2_665 0.96 2.97 3.696(5) 134 yes
C16 H16A Cg1 2_665 0.93 2.85 3.661(4) 146 yes
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
C2 O2 C3 O1 . . . . -67.6(7) ?
C2 O2 C3 C6 . . . . 166.3(6) ?
C1 O1 C3 O2 . . . . 87.6(6) ?
C1 O1 C3 C6 . . . . -147.2(5) ?
C4 O3 C5 O4 . . . . -3.6(11) ?
C4 O3 C5 C6 . . . . 173.0(5) ?
O2 C3 C6 C5 . . . . -53.2(6) ?
O1 C3 C6 C5 . . . . 179.1(5) ?
O2 C3 C6 C7 . . . . -179.9(4) ?
O1 C3 C6 C7 . . . . 52.5(6) ?
O4 C5 C6 C3 . . . . -54.2(10) ?
O3 C5 C6 C3 . . . . 129.3(6) ?
O4 C5 C6 C7 . . . . 76.8(8) ?
O3 C5 C6 C7 . . . . -99.7(6) ?
C3 C6 C7 C8 . . . . -128.5(4) ?
C5 C6 C7 C8 . . . . 103.3(5) ?
C3 C6 C7 C12 . . . . 53.2(6) ?
C5 C6 C7 C12 . . . . -75.0(6) ?
C12 C7 C8 C9 . . . . -1.1(6) ?
C6 C7 C8 C9 . . . . -179.5(4) ?
C12 C7 C8 O5 . . . . -173.1(3) ?
C6 C7 C8 O5 . . . . 8.4(5) ?
C13 O5 C8 C7 . . . . -114.9(4) ?
C13 O5 C8 C9 . . . . 72.8(5) ?
C7 C8 C9 C10 . . . . 1.4(6) ?
O5 C8 C9 C10 . . . . 173.3(3) ?
C8 C9 C10 C11 . . . . -1.0(6) ?
C9 C10 C11 C12 . . . . 0.4(7) ?
C8 C7 C12 C11 . . . . 0.5(6) ?
C6 C7 C12 C11 . . . . 178.8(4) ?
C10 C11 C12 C7 . . . . -0.1(7) ?
C8 O5 C13 N1 . . . . 12.4(6) ?
C8 O5 C13 C16 . . . . -169.3(4) ?
C14 N1 C13 O5 . . . . 178.4(4) ?
C14 N1 C13 C16 . . . . 0.2(6) ?
C15 N2 C14 N1 . . . . 0.9(8) ?
C13 N1 C14 N2 . . . . 0.0(8) ?
C14 N2 C15 C16 . . . . -2.0(7) ?
C14 N2 C15 Cl . . . . 177.9(4) ?
O5 C13 C16 C15 . . . . -179.4(4) ?
N1 C13 C16 C15 . . . . -1.2(7) ?
N2 C15 C16 C13 . . . . 2.2(7) ?
Cl C15 C16 C13 . . . . -177.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9188800
