#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/98/2209825.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_2209825
loop_
_publ_author_name
'Zheng-Bo Chen'
'Jun Wu'
'Pei-Zhi Zhang'
'Dong-Dong Wu'
_publ_section_title
;Methyl
 4-{2-chloro-4-[2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino]phenoxy}benzoate
;
_journal_coeditor_code           ER2005
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3285
_journal_page_last               o3286
_journal_paper_doi               10.1107/S1600536806025189
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C27 H24 Cl N3 O6'
_chemical_formula_moiety         'C27 H24 Cl N3 O6'
_chemical_formula_sum            'C27 H24 Cl N3 O6'
_chemical_formula_weight         521.94
_chemical_name_systematic
;
Methyl
4-{2-chloro-4-[2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino]phenoxy}benzoate
;
_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                98.02(3)
_cell_angle_beta                 116.33(3)
_cell_angle_gamma                94.746(19)
_cell_formula_units_Z            2
_cell_length_a                   10.763(4)
_cell_length_b                   11.066(6)
_cell_length_c                   12.051(4)
_cell_measurement_reflns_used    9127
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1256.8(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12447
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0464
_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)+(0.0686P)²+0.0343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                3660
_reflns_number_total             5677
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2005.cif
_cod_data_source_block           I
_cod_database_code               2209825
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
C C1 0.87879(16) 0.98627(15) 0.08243(14) 0.0445(4) Uani d . 1
C C2 0.93510(17) 0.87770(16) 0.09020(16) 0.0532(4) Uani d . 1
H H2 0.8775 0.8041 0.0392 0.064 Uiso calc R 1
C C3 1.07312(19) 0.87523(19) 0.17073(18) 0.0613(5) Uani d . 1
H H3 1.1081 0.8011 0.1729 0.074 Uiso calc R 1
C C4 1.15886(19) 0.9823(2) 0.24777(18) 0.0639(5) Uani d . 1
H H4 1.2519 0.9810 0.3041 0.077 Uiso calc R 1
C C5 1.1065(2) 1.0919(2) 0.24139(18) 0.0648(5) Uani d . 1
H H5 1.1644 1.1653 0.2928 0.078 Uiso calc R 1
C C6 0.96858(18) 1.09251(16) 0.15876(16) 0.0504(4) Uani d . 1
C C7 0.72800(17) 0.98752(17) -0.01013(16) 0.0557(4) Uani d . 1
H H7A 0.6953 1.0557 0.0234 0.067 Uiso calc R 1
H H7B 0.7249 1.0031 -0.0885 0.067 Uiso calc R 1
C C8 0.58037(15) 0.84621(16) 0.04219(14) 0.0475(4) Uani d . 1
C C9 0.61340(16) 0.92419(16) 0.15554(15) 0.0507(4) Uani d . 1
H H9 0.6770 0.9971 0.1821 0.061 Uiso calc R 1
C C10 0.55126(16) 0.89300(17) 0.22900(15) 0.0515(4) Uani d . 1
C C11 0.45984(16) 0.78475(17) 0.19410(16) 0.0526(4) Uani d . 1
C C12 0.42907(18) 0.70660(19) 0.08301(17) 0.0612(5) Uani d . 1
H H12 0.3679 0.6324 0.0584 0.073 Uiso calc R 1
C C13 0.48768(17) 0.73678(18) 0.00772(16) 0.0593(5) Uani d . 1
H H13 0.4648 0.6830 -0.0675 0.071 Uiso calc R 1
C C14 0.46471(16) 0.71844(16) 0.37519(16) 0.0505(4) Uani d . 1
C C15 0.40647(17) 0.72369(18) 0.45675(18) 0.0583(4) Uani d . 1
H H15 0.3210 0.7515 0.4348 0.070 Uiso calc R 1
C C16 0.47483(17) 0.68778(18) 0.57013(17) 0.0580(4) Uani d . 1
H H16 0.4356 0.6922 0.6252 0.070 Uiso calc R 1
C C17 0.60091(17) 0.64512(15) 0.60391(16) 0.0502(4) Uani d . 1
C C18 0.65664(17) 0.63829(17) 0.51941(16) 0.0545(4) Uani d . 1
H H18 0.7409 0.6084 0.5402 0.065 Uiso calc R 1
C C19 0.58984(18) 0.67471(17) 0.40602(17) 0.0558(4) Uani d . 1
H H19 0.6285 0.6700 0.3505 0.067 Uiso calc R 1
C C20 0.67387(19) 0.61081(17) 0.72866(17) 0.0579(4) Uani d . 1
C C21 0.8692(3) 0.5286(3) 0.8627(2) 0.0882(7) Uani d . 1
H H21A 0.8909 0.5973 0.9300 0.132 Uiso calc R 1
H H21B 0.9549 0.5056 0.8666 0.132 Uiso calc R 1
H H21C 0.8158 0.4599 0.8712 0.132 Uiso calc R 1
C C22 0.89913(17) 1.27048(17) 0.23502(18) 0.0564(4) Uani d . 1
C C23 0.83710(18) 1.44241(18) 0.3008(2) 0.0699(6) Uani d . 1
C C24 0.8481(2) 1.4001(2) 0.4053(3) 0.0827(7) Uani d . 1
H H24 0.8273 1.4451 0.4643 0.099 Uiso calc R 1
C C25 0.8913(2) 1.2884(2) 0.4187(2) 0.0706(5) Uani d . 1
C C26 0.7998(3) 1.6049(3) 0.1866(3) 0.1100(10) Uani d . 1
H H26A 0.8911 1.6080 0.1905 0.165 Uiso calc R 1
H H26B 0.7775 1.6870 0.1928 0.165 Uiso calc R 1
H H26C 0.7310 1.5543 0.1079 0.165 Uiso calc R 1
C C27 0.9717(3) 1.1364(3) 0.5408(3) 0.1038(9) Uani d . 1
H H27A 0.9146 1.0705 0.4702 0.156 Uiso calc R 1
H H27B 0.9778 1.1135 0.6169 0.156 Uiso calc R 1
H H27C 1.0641 1.1514 0.5476 0.156 Uiso calc R 1
N N1 0.63285(14) 0.87581(15) -0.03773(13) 0.0582(4) Uani d . 1
H H1 0.6114 0.8150 -0.1067 0.080 Uiso d R 1
N N2 0.86317(15) 1.37949(14) 0.21278(16) 0.0628(4) Uani d . 1
N N3 0.91562(15) 1.21978(14) 0.33237(16) 0.0611(4) Uani d . 1
O O1 0.39010(11) 0.75721(13) 0.26375(12) 0.0623(3) Uani d . 1
O O2 0.78841(14) 0.56315(14) 0.74323(12) 0.0710(4) Uani d . 1
O O3 0.63775(17) 0.62523(16) 0.80939(14) 0.0860(5) Uani d . 1
O O4 0.91852(15) 1.20546(12) 0.14222(12) 0.0678(4) Uani d . 1
O O5 0.79957(16) 1.55387(14) 0.28751(19) 0.0938(5) Uani d . 1
O O6 0.9099(2) 1.24607(17) 0.52271(17) 0.0968(5) Uani d . 1
Cl Cl1 0.58494(6) 0.99567(6) 0.36445(5) 0.0860(2) Uani d . 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
_geom_angle_publ_flag
C6 C1 C2 116.62(15) ?
C6 C1 C7 122.04(15) ?
C2 C1 C7 121.27(16) ?
C3 C2 C1 122.18(17) ?
C3 C2 H2 118.9 ?
C1 C2 H2 118.9 ?
C4 C3 C2 119.71(18) ?
C4 C3 H3 120.1 ?
C2 C3 H3 120.1 ?
C3 C4 C5 119.52(17) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
C6 C5 C4 119.78(18) ?
C6 C5 H5 120.1 ?
C4 C5 H5 120.1 ?
C1 C6 C5 122.15(17) ?
C1 C6 O4 117.65(15) ?
C5 C6 O4 119.97(17) ?
N1 C7 C1 114.91(14) ?
N1 C7 H7A 108.5 ?
C1 C7 H7A 108.5 ?
N1 C7 H7B 108.5 ?
C1 C7 H7B 108.5 ?
H7A C7 H7B 107.5 ?
N1 C8 C13 119.56(15) ?
N1 C8 C9 122.24(16) ?
C13 C8 C9 118.17(16) ?
C10 C9 C8 119.80(16) ?
C10 C9 H9 120.1 ?
C8 C9 H9 120.1 ?
C11 C10 C9 121.56(16) ?
C11 C10 Cl1 119.28(14) ?
C9 C10 Cl1 119.12(14) ?
C10 C11 C12 118.61(17) ?
C10 C11 O1 121.49(16) ?
C12 C11 O1 119.73(16) ?
C11 C12 C13 120.76(18) ?
C11 C12 H12 119.6 ?
C13 C12 H12 119.6 ?
C12 C13 C8 121.09(17) ?
C12 C13 H13 119.5 ?
C8 C13 H13 119.5 ?
O1 C14 C15 116.19(14) ?
O1 C14 C19 123.47(15) ?
C15 C14 C19 120.33(17) ?
C16 C15 C14 119.79(16) ?
C16 C15 H15 120.1 ?
C14 C15 H15 120.1 ?
C15 C16 C17 121.03(16) ?
C15 C16 H16 119.5 ?
C17 C16 H16 119.5 ?
C16 C17 C18 118.34(16) ?
C16 C17 C20 119.54(16) ?
C18 C17 C20 122.11(15) ?
C19 C18 C17 121.23(16) ?
C19 C18 H18 119.4 ?
C17 C18 H18 119.4 ?
C18 C19 C14 119.26(16) ?
C18 C19 H19 120.4 ?
C14 C19 H19 120.4 ?
O3 C20 O2 122.78(18) ?
O3 C20 C17 125.04(18) ?
O2 C20 C17 112.17(16) ?
O2 C21 H21A 109.5 ?
O2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
N3 C22 N2 128.71(18) y
N3 C22 O4 118.24(16) ?
N2 C22 O4 113.04(17) ?
N2 C23 O5 118.7(2) ?
N2 C23 C24 123.59(19) y
O5 C23 C24 117.7(2) ?
C25 C24 C23 116.4(2) y
C25 C24 H24 121.8 ?
C23 C24 H24 121.8 ?
N3 C25 O6 118.9(2) ?
N3 C25 C24 122.7(2) y
O6 C25 C24 118.4(2) ?
O5 C26 H26A 109.5 ?
O5 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
O5 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
O6 C27 H27A 109.5 ?
O6 C27 H27B 109.5 ?
H27A C27 H27B 109.5 ?
O6 C27 H27C 109.5 ?
H27A C27 H27C 109.5 ?
H27B C27 H27C 109.5 ?
C8 N1 C7 123.23(15) ?
C8 N1 H1 115.5 ?
C7 N1 H1 120.9 ?
C22 N2 C23 113.74(18) y
C22 N3 C25 114.73(17) y
C14 O1 C11 118.05(12) ?
C20 O2 C21 116.80(17) ?
C22 O4 C6 118.89(14) ?
C23 O5 C26 118.9(2) ?
C25 O6 C27 116.68(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.373(2) ?
C1 C2 1.386(2) ?
C1 C7 1.510(2) ?
C2 C3 1.373(2) ?
C2 H2 0.9300 ?
C3 C4 1.367(3) ?
C3 H3 0.9300 ?
C4 C5 1.377(3) ?
C4 H4 0.9300 ?
C5 C6 1.374(3) ?
C5 H5 0.9300 ?
C6 O4 1.406(2) ?
C7 N1 1.436(2) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N1 1.376(2) ?
C8 C13 1.388(3) ?
C8 C9 1.388(2) ?
C9 C10 1.386(2) ?
C9 H9 0.9300 ?
C10 C11 1.370(3) ?
C10 Cl1 1.7253(19) y
C11 C12 1.373(3) ?
C11 O1 1.398(2) ?
C12 C13 1.375(3) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 O1 1.376(2) ?
C14 C15 1.378(2) ?
C14 C19 1.378(2) ?
C15 C16 1.369(3) ?
C15 H15 0.9300 ?
C16 C17 1.378(2) ?
C16 H16 0.9300 ?
C17 C18 1.389(2) ?
C17 C20 1.477(3) ?
C18 C19 1.370(2) ?
C18 H18 0.9300 ?
C19 H19 0.9300 ?
C20 O3 1.194(2) ?
C20 O2 1.330(2) ?
C21 O2 1.440(2) ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
C22 N3 1.318(2) y
C22 N2 1.324(2) y
C22 O4 1.349(2) y
C23 N2 1.334(3) y
C23 O5 1.338(3) ?
C23 C24 1.364(3) y
C24 C25 1.362(3) y
C24 H24 0.9300 ?
C25 N3 1.334(3) y
C25 O6 1.337(3) ?
C26 O5 1.411(3) ?
C26 H26A 0.9600 ?
C26 H26B 0.9600 ?
C26 H26C 0.9600 ?
C27 O6 1.429(3) ?
C27 H27A 0.9600 ?
C27 H27B 0.9600 ?
C27 H27C 0.9600 ?
N1 H1 0.9192 ?
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
N1 H1 O3 1_554 0.92 2.30 3.126(3) 150 y
C7 H7A O4 . 0.97 2.49 2.828(3) 100 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127762
