#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/78/2207808.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_2207808
loop_
_publ_author_name
'Yong-Hong Wen'
'Li-Li Xu'
'Shu-Sheng Zhang'
'Xue-Mei Li'
_publ_section_title
;
 N-(4-Ethoxyphenyl)-2-(quinolin-8-yloxy)acetamide
;
_journal_coeditor_code           IS6167
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o253
_journal_page_last               o254
_journal_paper_doi               10.1107/S1600536805041498
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H18 N2 O3'
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_chemical_name_systematic
;
N-(4-Ethoxyphenyl)-2-(quinolin-8-yloxy)acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.676(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0480(13)
_cell_length_b                   8.5248(14)
_cell_length_c                   23.821(4)
_cell_measurement_reflns_used    4032
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.5
_cell_volume                     1633.6(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8662
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0428
_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)+(0.0629P)²+0.1712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2658
_reflns_number_total             3220
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6167.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207808
_cod_database_fobs_code          2207808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.00672(11) 0.97193(11) 0.17553(4) 0.0618(3) Uani d . 1 O
O2 -0.34476(13) 1.04045(18) 0.08714(5) 0.0981(4) Uani d . 1 O
O3 0.12585(11) 0.72344(11) 0.03623(4) 0.0635(3) Uani d . 1 O
N1 0.31135(14) 0.86038(14) 0.19635(5) 0.0629(3) Uani d . 1 N
N2 -0.10480(12) 0.90637(13) 0.07366(4) 0.0545(3) Uani d . 1 N
H2A -0.0122 0.8819 0.0904 0.065 Uiso calc R 1 H
C1 0.46017(19) 0.80453(19) 0.20778(7) 0.0753(4) Uani d . 1 C
H1B 0.5164 0.7578 0.1786 0.090 Uiso calc R 1 H
C2 0.5411(2) 0.8098(2) 0.26068(8) 0.0816(5) Uani d . 1 C
H2B 0.6467 0.7671 0.2661 0.098 Uiso calc R 1 H
C3 0.4622(2) 0.87854(18) 0.30357(7) 0.0759(4) Uani d . 1 C
H3A 0.5131 0.8827 0.3391 0.091 Uiso calc R 1 H
C4 0.30231(18) 0.94401(15) 0.29442(6) 0.0602(3) Uani d . 1 C
C5 0.2135(2) 1.02087(18) 0.33659(6) 0.0723(4) Uani d . 1 C
H5A 0.2605 1.0315 0.3725 0.087 Uiso calc R 1 H
C6 0.0597(2) 1.07919(18) 0.32484(6) 0.0731(4) Uani d . 1 C
H6A 0.0023 1.1295 0.3530 0.088 Uiso calc R 1 H
C7 -0.01450(19) 1.06512(17) 0.27099(6) 0.0646(4) Uani d . 1 C
H7A -0.1204 1.1053 0.2639 0.078 Uiso calc R 1 H
C8 0.06862(17) 0.99234(14) 0.22890(5) 0.0540(3) Uani d . 1 C
C9 0.23151(16) 0.93046(14) 0.23956(5) 0.0534(3) Uani d . 1 C
C10 -0.15166(16) 1.03701(18) 0.16219(6) 0.0643(4) Uani d . 1 C
H10A -0.1461 1.1503 0.1657 0.077 Uiso calc R 1 H
H10B -0.2316 0.9987 0.1886 0.077 Uiso calc R 1 H
C11 -0.20894(16) 0.99435(17) 0.10340(6) 0.0617(3) Uani d . 1 C
C12 -0.12822(14) 0.84898(15) 0.01848(5) 0.0511(3) Uani d . 1 C
C13 -0.26282(16) 0.88459(18) -0.01681(6) 0.0633(4) Uani d . 1 C
H13A -0.3470 0.9491 -0.0042 0.076 Uiso calc R 1 H
C14 -0.27254(18) 0.8247(2) -0.07067(6) 0.0712(4) Uani d . 1 C
H14A -0.3629 0.8498 -0.0942 0.085 Uiso calc R 1 H
C15 -0.15032(18) 0.72893(19) -0.08964(6) 0.0708(4) Uani d . 1 C
H15A -0.1578 0.6890 -0.1260 0.085 Uiso calc R 1 H
C16 -0.01518(17) 0.69105(18) -0.05485(6) 0.0649(4) Uani d . 1 C
H16A 0.0674 0.6249 -0.0677 0.078 Uiso calc R 1 H
C17 -0.00300(15) 0.75117(15) -0.00128(5) 0.0533(3) Uani d . 1 C
C18 0.27288(17) 0.65097(19) 0.01583(6) 0.0661(4) Uani d . 1 C
H18A 0.3119 0.7071 -0.0167 0.079 Uiso calc R 1 H
H18B 0.2503 0.5432 0.0050 0.079 Uiso calc R 1 H
C19 0.40048(19) 0.6567(2) 0.06267(7) 0.0825(5) Uani d . 1 C
H19A 0.5016 0.6091 0.0507 0.124 Uiso calc R 1 H
H19B 0.3603 0.6007 0.0945 0.124 Uiso calc R 1 H
H19C 0.4215 0.7639 0.0729 0.124 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
C8 O1 C10 117.44(10)
C17 O3 C18 118.06(10)
C1 N1 C9 116.71(13)
C11 N2 C12 128.12(11)
C11 N2 H2A 115.9
C12 N2 H2A 115.9
N1 C1 C2 124.95(15)
N1 C1 H1B 117.5
C2 C1 H1B 117.5
C3 C2 C1 118.46(15)
C3 C2 H2B 120.8
C1 C2 H2B 120.8
C2 C3 C4 120.02(14)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
C5 C4 C3 123.45(14)
C5 C4 C9 119.78(14)
C3 C4 C9 116.77(14)
C6 C5 C4 120.11(14)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C5 C6 C7 121.26(14)
C5 C6 H6A 119.4
C7 C6 H6A 119.4
C8 C7 C6 120.23(14)
C8 C7 H7A 119.9
C6 C7 H7A 119.9
O1 C8 C7 124.58(13)
O1 C8 C9 115.28(11)
C7 C8 C9 120.15(12)
N1 C9 C4 123.07(12)
N1 C9 C8 118.47(11)
C4 C9 C8 118.46(12)
O1 C10 C11 111.27(11)
O1 C10 H10A 109.4
C11 C10 H10A 109.4
O1 C10 H10B 109.4
C11 C10 H10B 109.4
H10A C10 H10B 108.0
O2 C11 N2 125.64(14)
O2 C11 C10 117.82(12)
N2 C11 C10 116.54(11)
C13 C12 C17 118.96(12)
C13 C12 N2 124.79(12)
C17 C12 N2 116.24(10)
C14 C13 C12 120.32(13)
C14 C13 H13A 119.8
C12 C13 H13A 119.8
C15 C14 C13 120.45(13)
C15 C14 H14A 119.8
C13 C14 H14A 119.8
C14 C15 C16 120.11(14)
C14 C15 H15A 119.9
C16 C15 H15A 119.9
C17 C16 C15 120.07(14)
C17 C16 H16A 120.0
C15 C16 H16A 120.0
O3 C17 C16 124.95(12)
O3 C17 C12 114.97(11)
C16 C17 C12 120.08(12)
O3 C18 C19 106.79(11)
O3 C18 H18A 110.4
C19 C18 H18A 110.4
O3 C18 H18B 110.4
C19 C18 H18B 110.4
H18A C18 H18B 108.6
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 1.3631(15) yes
O1 C10 1.4176(15) yes
O2 C11 1.2142(16) yes
O3 C17 1.3695(15) ?
O3 C18 1.4324(15) ?
N1 C1 1.3100(18) ?
N1 C9 1.3667(17) ?
N2 C11 1.3422(16) yes
N2 C12 1.4101(15) yes
N2 H2A 0.8600 ?
C1 C2 1.402(2) ?
C1 H1B 0.9300 ?
C2 C3 1.352(2) ?
C2 H2B 0.9300 ?
C3 C4 1.413(2) ?
C3 H3A 0.9300 ?
C4 C5 1.411(2) ?
C4 C9 1.4149(18) ?
C5 C6 1.355(2) ?
C5 H5A 0.9300 ?
C6 C7 1.404(2) ?
C6 H6A 0.9300 ?
C7 C8 1.3701(18) ?
C7 H7A 0.9300 ?
C8 C9 1.4289(18) ?
C10 C11 1.506(2) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C12 C13 1.3853(17) ?
C12 C17 1.4001(18) ?
C13 C14 1.381(2) ?
C13 H13A 0.9300 ?
C14 C15 1.365(2) ?
C14 H14A 0.9300 ?
C15 C16 1.3861(19) ?
C15 H15A 0.9300 ?
C16 C17 1.3760(19) ?
C16 H16A 0.9300 ?
C18 C19 1.495(2) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 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 O1 1_555 0.86 2.17 2.6230(10) 112 yes
N2 H2A O3 1_555 0.86 2.19 2.6020(10) 109 yes
C13 H13A O2 1_555 0.93 2.31 2.903(2) 121 yes
C14 H14A O2 3_475 0.93 2.54 3.300(2) 139 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
C9 N1 C1 C2 0.9(2)
N1 C1 C2 C3 -0.6(3)
C1 C2 C3 C4 -0.5(2)
C2 C3 C4 C5 -178.47(15)
C2 C3 C4 C9 1.2(2)
C3 C4 C5 C6 -179.23(14)
C9 C4 C5 C6 1.1(2)
C4 C5 C6 C7 -0.1(2)
C5 C6 C7 C8 -0.4(2)
C10 O1 C8 C7 3.00(19)
C10 O1 C8 C9 -177.43(11)
C6 C7 C8 O1 179.48(12)
C6 C7 C8 C9 -0.1(2)
C1 N1 C9 C4 -0.03(19)
C1 N1 C9 C8 -179.74(13)
C5 C4 C9 N1 178.71(12)
C3 C4 C9 N1 -0.98(19)
C5 C4 C9 C8 -1.57(18)
C3 C4 C9 C8 178.74(12)
O1 C8 C9 N1 1.20(17)
C7 C8 C9 N1 -179.20(12)
O1 C8 C9 C4 -178.53(10)
C7 C8 C9 C4 1.07(18)
C8 O1 C10 C11 -175.60(11)
C12 N2 C11 O2 0.0(2)
C12 N2 C11 C10 179.20(12)
O1 C10 C11 O2 178.58(14)
O1 C10 C11 N2 -0.69(19)
C11 N2 C12 C13 4.9(2)
C11 N2 C12 C17 -176.13(13)
C17 C12 C13 C14 -0.2(2)
N2 C12 C13 C14 178.68(13)
C12 C13 C14 C15 0.4(2)
C13 C14 C15 C16 0.0(2)
C14 C15 C16 C17 -0.7(2)
C18 O3 C17 C16 12.0(2)
C18 O3 C17 C12 -167.92(12)
C15 C16 C17 O3 -178.99(13)
C15 C16 C17 C12 0.9(2)
C13 C12 C17 O3 179.44(11)
N2 C12 C17 O3 0.45(17)
C13 C12 C17 C16 -0.4(2)
N2 C12 C17 C16 -179.44(12)
C17 O3 C18 C19 171.70(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6201401
