#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/75/2207578.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_2207578
loop_
_publ_author_name
'Yong-Hong Wen'
'Xue-Mei Li'
'Shu-Sheng Zhang'
'Mao-Jie Li'
_publ_section_title
2-[N-(2-Ethoxyphenyl)carbamoylmethoxy]-N-(2-pyridylmethyl)benzamide
_journal_coeditor_code           IS6157
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4333
_journal_page_last               o4335
_journal_paper_doi               10.1107/S1600536805038614
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C23 H23 N3 O4'
_chemical_formula_moiety         'C23 H23 N3 O4'
_chemical_formula_sum            'C23 H23 N3 O4'
_chemical_formula_weight         405.44
_chemical_name_systematic
;
2-[N-(2-Ethoxyphenyl)carbamoylmethoxy]-N-(2-pyridylmethyl)benzamide
;
_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           SHELXL97
_cell_angle_alpha                106.481(3)
_cell_angle_beta                 90.471(3)
_cell_angle_gamma                100.828(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7109(14)
_cell_length_b                   10.8764(17)
_cell_length_c                   11.2510(18)
_cell_measurement_reflns_used    1716
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.3
_cell_volume                     1001.8(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5693
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.89
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0516
_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)+(0.0469P)²+0.197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2986
_reflns_number_total             3863
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6157.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2207578
_cod_database_fobs_code          2207578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O1 0.69091(19) -0.06042(16) 0.41724(15) 0.0741(5) Uani d . 1 O
O2 0.43012(16) 0.03107(12) 0.15861(11) 0.0493(3) Uani d . 1 O
O3 0.27117(18) -0.17145(13) -0.00895(13) 0.0590(4) Uani d . 1 O
O4 -0.00946(15) 0.03480(12) -0.24412(11) 0.0506(4) Uani d . 1 O
C3 0.7448(3) -0.5204(2) 0.0285(2) 0.0671(6) Uani d . 1 C
H3A 0.7540 -0.6072 0.0141 0.081 Uiso calc R 1 H
N2 0.52390(19) -0.14435(15) 0.24957(14) 0.0475(4) Uani d . 1 N
H2A 0.4634 -0.1294 0.1967 0.057 Uiso calc R 1 H
N3 0.17318(17) -0.04732(14) -0.11231(13) 0.0418(4) Uani d . 1 N
H3B 0.1760 0.0328 -0.1101 0.050 Uiso calc R 1 H
C4 0.6529(3) -0.46523(19) 0.1186(2) 0.0601(6) Uani d . 1 C
H4A 0.5989 -0.5147 0.1659 0.072 Uiso calc R 1 H
C2 0.8227(3) -0.4457(2) -0.0398(2) 0.0638(6) Uani d . 1 C
H2B 0.8852 -0.4804 -0.1022 0.077 Uiso calc R 1 H
C1 0.8058(3) -0.3185(2) -0.0135(2) 0.0611(6) Uani d . 1 C
H1A 0.8597 -0.2676 -0.0595 0.073 Uiso calc R 1 H
N1 0.7170(2) -0.26223(15) 0.07411(15) 0.0501(4) Uani d . 1 N
C5 0.6405(2) -0.33576(17) 0.13931(17) 0.0441(4) Uani d . 1 C
C6 0.5380(3) -0.27722(19) 0.23830(19) 0.0551(5) Uani d . 1 C
H6A 0.4339 -0.3318 0.2216 0.066 Uiso calc R 1 H
H6B 0.5789 -0.2802 0.3177 0.066 Uiso calc R 1 H
C7 0.6033(2) -0.04364(19) 0.34088(17) 0.0452(4) Uani d . 1 C
C8 0.5804(2) 0.09288(18) 0.34938(16) 0.0420(4) Uani d . 1 C
C9 0.6493(2) 0.1908(2) 0.45384(18) 0.0558(5) Uani d . 1 C
H9A 0.7045 0.1688 0.5133 0.067 Uiso calc R 1 H
C10 0.6389(3) 0.3194(2) 0.47286(19) 0.0614(6) Uani d . 1 C
H10A 0.6860 0.3829 0.5443 0.074 Uiso calc R 1 H
C11 0.5590(3) 0.3531(2) 0.38586(19) 0.0580(5) Uani d . 1 C
H11A 0.5521 0.4400 0.3979 0.070 Uiso calc R 1 H
C12 0.4885(2) 0.25873(19) 0.28029(18) 0.0506(5) Uani d . 1 C
H12A 0.4345 0.2822 0.2212 0.061 Uiso calc R 1 H
C13 0.4981(2) 0.12921(17) 0.26206(15) 0.0402(4) Uani d . 1 C
C14 0.3334(2) 0.06154(17) 0.07408(16) 0.0418(4) Uani d . 1 C
H14A 0.3952 0.1192 0.0328 0.050 Uiso calc R 1 H
H14B 0.2539 0.1052 0.1175 0.050 Uiso calc R 1 H
C15 0.2576(2) -0.06568(17) -0.01981(16) 0.0398(4) Uani d . 1 C
C16 0.0808(2) -0.14259(17) -0.21220(15) 0.0394(4) Uani d . 1 C
C17 0.0799(2) -0.27544(18) -0.24339(17) 0.0484(5) Uani d . 1 C
H17A 0.1422 -0.3073 -0.1963 0.058 Uiso calc R 1 H
C18 -0.0132(2) -0.3610(2) -0.34425(19) 0.0568(5) Uani d . 1 C
H18A -0.0138 -0.4501 -0.3643 0.068 Uiso calc R 1 H
C19 -0.1044(3) -0.3149(2) -0.4147(2) 0.0605(6) Uani d . 1 C
H19A -0.1661 -0.3731 -0.4827 0.073 Uiso calc R 1 H
C20 -0.1056(2) -0.1829(2) -0.38562(18) 0.0532(5) Uani d . 1 C
H20A -0.1675 -0.1522 -0.4340 0.064 Uiso calc R 1 H
C21 -0.0141(2) -0.09658(18) -0.28416(16) 0.0422(4) Uani d . 1 C
C22 -0.0884(3) 0.0909(2) -0.32134(18) 0.0551(5) Uani d . 1 C
H22A -0.1995 0.0533 -0.3309 0.066 Uiso calc R 1 H
H22B -0.0471 0.0733 -0.4030 0.066 Uiso calc R 1 H
C23 -0.0624(3) 0.2350(2) -0.2608(2) 0.0738(7) Uani d . 1 C
H23A -0.1132 0.2750 -0.3116 0.111 Uiso calc R 1 H
H23B 0.0479 0.2711 -0.2510 0.111 Uiso calc R 1 H
H23C -0.1053 0.2515 -0.1808 0.111 Uiso calc R 1 H
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
_geom_angle_publ_flag
C13 O2 C14 118.57(13) ?
C21 O4 C22 117.78(14) ?
C2 C3 C4 118.84(19) ?
C2 C3 H3A 120.6 ?
C4 C3 H3A 120.6 ?
C7 N2 C6 121.29(16) yes
C7 N2 H2A 119.4 ?
C6 N2 H2A 119.4 ?
C15 N3 C16 128.42(15) yes
C15 N3 H3B 115.8 ?
C16 N3 H3B 115.8 ?
C3 C4 C5 120.0(2) ?
C3 C4 H4A 120.0 ?
C5 C4 H4A 120.0 ?
C3 C2 C1 117.9(2) ?
C3 C2 H2B 121.1 ?
C1 C2 H2B 121.1 ?
N1 C1 C2 124.5(2) ?
N1 C1 H1A 117.8 ?
C2 C1 H1A 117.8 ?
C5 N1 C1 117.29(16) ?
N1 C5 C4 121.54(18) ?
N1 C5 C6 119.32(16) ?
C4 C5 C6 119.14(17) ?
N2 C6 C5 115.91(16) ?
N2 C6 H6A 108.3 ?
C5 C6 H6A 108.3 ?
N2 C6 H6B 108.3 ?
C5 C6 H6B 108.3 ?
H6A C6 H6B 107.4 ?
O1 C7 N2 121.45(18) ?
O1 C7 C8 119.87(18) ?
N2 C7 C8 118.67(15) ?
C9 C8 C13 117.35(18) ?
C9 C8 C7 116.24(17) ?
C13 C8 C7 126.41(16) ?
C10 C9 C8 122.34(19) ?
C10 C9 H9A 118.8 ?
C8 C9 H9A 118.8 ?
C11 C10 C9 119.41(19) ?
C11 C10 H10A 120.3 ?
C9 C10 H10A 120.3 ?
C10 C11 C12 120.24(19) ?
C10 C11 H11A 119.9 ?
C12 C11 H11A 119.9 ?
C11 C12 C13 120.13(19) ?
C11 C12 H12A 119.9 ?
C13 C12 H12A 119.9 ?
O2 C13 C12 122.62(16) ?
O2 C13 C8 116.86(15) ?
C12 C13 C8 120.52(17) ?
O2 C14 C15 107.39(14) ?
O2 C14 H14A 110.2 ?
C15 C14 H14A 110.2 ?
O2 C14 H14B 110.2 ?
C15 C14 H14B 110.2 ?
H14A C14 H14B 108.5 ?
O3 C15 N3 125.36(17) ?
O3 C15 C14 122.11(16) ?
N3 C15 C14 112.51(14) ?
C17 C16 C21 119.00(17) ?
C17 C16 N3 124.60(16) ?
C21 C16 N3 116.40(15) ?
C18 C17 C16 120.29(18) ?
C18 C17 H17A 119.9 ?
C16 C17 H17A 119.9 ?
C19 C18 C17 120.28(19) ?
C19 C18 H18A 119.9 ?
C17 C18 H18A 119.9 ?
C18 C19 C20 120.56(19) ?
C18 C19 H19A 119.7 ?
C20 C19 H19A 119.7 ?
C19 C20 C21 119.65(19) ?
C19 C20 H20A 120.2 ?
C21 C20 H20A 120.2 ?
O4 C21 C20 124.95(17) ?
O4 C21 C16 114.83(15) ?
C20 C21 C16 120.21(17) ?
O4 C22 C23 107.97(16) ?
O4 C22 H22A 110.1 ?
C23 C22 H22A 110.1 ?
O4 C22 H22B 110.1 ?
C23 C22 H22B 110.1 ?
H22A C22 H22B 108.4 ?
C22 C23 H23A 109.5 ?
C22 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C22 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.218(2) yes
O2 C13 1.375(2) yes
O2 C14 1.4126(19) yes
O3 C15 1.218(2) yes
O4 C21 1.363(2) yes
O4 C22 1.431(2) yes
C3 C2 1.366(3) ?
C3 C4 1.370(3) ?
C3 H3A 0.9300 ?
N2 C7 1.341(2) yes
N2 C6 1.443(2) yes
N2 H2A 0.8600 ?
N3 C15 1.351(2) yes
N3 C16 1.413(2) yes
N3 H3B 0.8600 ?
C4 C5 1.386(3) ?
C4 H4A 0.9300 ?
C2 C1 1.367(3) ?
C2 H2B 0.9300 ?
C1 N1 1.339(2) ?
C1 H1A 0.9300 ?
N1 C5 1.327(2) ?
C5 C6 1.507(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.512(3) ?
C8 C9 1.383(3) ?
C8 C13 1.397(2) ?
C9 C10 1.374(3) ?
C9 H9A 0.9300 ?
C10 C11 1.366(3) ?
C10 H10A 0.9300 ?
C11 C12 1.379(3) ?
C11 H11A 0.9300 ?
C12 C13 1.383(3) ?
C12 H12A 0.9300 ?
C14 C15 1.511(3) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C16 C17 1.385(2) ?
C16 C21 1.401(2) ?
C17 C18 1.383(3) ?
C17 H17A 0.9300 ?
C18 C19 1.369(3) ?
C18 H18A 0.9300 ?
C19 C20 1.382(3) ?
C19 H19A 0.9300 ?
C20 C21 1.384(3) ?
C20 H20A 0.9300 ?
C22 C23 1.493(3) ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
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
N2 H2A O2 1_555 0.86 1.98 2.652(2) 134 yes
N3 H3B O4 1_555 0.86 2.21 2.603(2) 108 yes
N3 H3B N1 2_655 0.86 2.41 3.224(2) 158 yes
C3 H3A O3 2_645 0.93 2.36 3.272(3) 166 yes
C6 H6B O1 1_555 0.97 2.35 2.733(3) 103 yes
C9 H9A O1 1_555 0.93 2.40 2.739(3) 101 yes
C14 H14A N1 2_655 0.97 2.54 3.186(3) 124 yes
C17 H17A O3 1_555 0.93 2.34 2.922(2) 121 yes
C23 H23B Cg1 2_655 0.96 2.73 3.546(3) 136 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
C2 C3 C4 C5 -0.1(3)
C4 C3 C2 C1 0.6(3)
C3 C2 C1 N1 -0.6(4)
C2 C1 N1 C5 0.0(3)
C1 N1 C5 C4 0.5(3)
C1 N1 C5 C6 -179.53(18)
C3 C4 C5 N1 -0.5(3)
C3 C4 C5 C6 179.6(2)
C7 N2 C6 C5 -102.4(2)
N1 C5 C6 N2 3.5(3)
C4 C5 C6 N2 -176.60(18)
C6 N2 C7 O1 0.4(3)
C6 N2 C7 C8 -178.52(16)
O1 C7 C8 C9 -6.9(3)
N2 C7 C8 C9 172.08(17)
O1 C7 C8 C13 172.59(18)
N2 C7 C8 C13 -8.5(3)
C13 C8 C9 C10 -0.1(3)
C7 C8 C9 C10 179.38(18)
C8 C9 C10 C11 -0.4(3)
C9 C10 C11 C12 0.4(3)
C10 C11 C12 C13 0.2(3)
C14 O2 C13 C12 -6.7(3)
C14 O2 C13 C8 173.98(15)
C11 C12 C13 O2 180.00(17)
C11 C12 C13 C8 -0.7(3)
C9 C8 C13 O2 -179.99(16)
C7 C8 C13 O2 0.5(3)
C9 C8 C13 C12 0.7(3)
C7 C8 C13 C12 -178.77(17)
C13 O2 C14 C15 -172.42(14)
C16 N3 C15 O3 2.0(3)
C16 N3 C15 C14 -176.63(16)
O2 C14 C15 O3 7.1(2)
O2 C14 C15 N3 -174.30(14)
C15 N3 C16 C17 -10.5(3)
C15 N3 C16 C21 170.32(16)
C21 C16 C17 C18 0.1(3)
N3 C16 C17 C18 -179.05(17)
C16 C17 C18 C19 0.5(3)
C17 C18 C19 C20 -0.4(3)
C18 C19 C20 C21 -0.2(3)
C22 O4 C21 C20 -8.7(3)
C22 O4 C21 C16 172.58(15)
C19 C20 C21 O4 -177.79(18)
C19 C20 C21 C16 0.9(3)
C17 C16 C21 O4 177.98(16)
N3 C16 C21 O4 -2.8(2)
C17 C16 C21 C20 -0.8(3)
N3 C16 C21 C20 178.44(16)
C21 O4 C22 C23 -178.11(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126862
