#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226989.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_2226989
loop_
_publ_author_name
'Wang, Yuan'
'Li, Yan-Wei'
'Li, Xiao-Xia'
_publ_section_title
;
 N-(4-Chlorophenyl)-2-(8-quinolyloxy)acetamide monohydrate
;
_journal_coeditor_code           LH5076
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1977
_journal_paper_doi               10.1107/S1600536810026206
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H13 Cl N2 O2, H2 O'
_chemical_formula_moiety         'C17 H13 Cl N2 O2, H2 O'
_chemical_formula_sum            'C17 H15 Cl N2 O3'
_chemical_formula_weight         330.76
_chemical_name_systematic
;
N-(4-Chlorophenyl)-2-(8-quinolyloxy)acetamide monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.4984(19)
_cell_length_b                   5.2601(6)
_cell_length_c                   29.851(3)
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.85
_cell_measurement_theta_min      2.50
_cell_volume                     3061.6(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            15222
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0471
_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)+(0.0548P)²+0.0231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                1800
_reflns_number_total             3622
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5076.cif
_cod_data_source_block           I
_cod_original_cell_volume        3061.7(5)
_cod_database_code               2226989
_cod_database_fobs_code          2226989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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 Cl1 0.32260(4) 0.36909(15) 0.044180(19) 0.0858(3) Uani d . 1 . .
O O2 0.40858(7) 0.1726(3) 0.32297(4) 0.0532(4) Uani d . 1 . .
N N2 0.34502(9) 0.5390(3) 0.36817(6) 0.0505(5) Uani d . 1 . .
N N1 0.38877(10) 0.1567(3) 0.23341(6) 0.0524(5) Uani d D 1 . .
C C10 0.47572(12) 0.0589(4) 0.38814(7) 0.0568(6) Uani d . 1 . .
H H10 0.4991 -0.0675 0.3726 0.068 Uiso calc R 1 . .
C C17 0.39211(11) 0.3959(4) 0.39023(6) 0.0454(5) Uani d . 1 . .
C C13 0.40699(12) 0.4337(4) 0.43606(7) 0.0522(6) Uani d . 1 . .
C C7 0.42016(11) -0.0454(4) 0.25142(7) 0.0506(6) Uani d . 1 . .
C C9 0.42715(11) 0.2012(4) 0.36669(6) 0.0470(5) Uani d . 1 . .
C C11 0.49027(12) 0.1029(5) 0.43328(8) 0.0647(7) Uani d . 1 . .
H H11 0.5238 0.0060 0.4474 0.078 Uiso calc R 1 . .
C C12 0.45676(13) 0.2827(4) 0.45688(7) 0.0618(7) Uani d . 1 . .
H H12 0.4667 0.3065 0.4871 0.074 Uiso calc R 1 . .
C C14 0.37041(14) 0.6238(5) 0.45851(7) 0.0650(7) Uani d . 1 . .
H H14 0.3782 0.6522 0.4888 0.078 Uiso calc R 1 . .
O O1 0.43645(9) -0.2349(3) 0.23095(5) 0.0771(5) Uani d . 1 . .
C C1 0.34138(12) 0.3011(5) 0.09954(7) 0.0564(6) Uani d . 1 . .
C C8 0.43823(12) -0.0380(4) 0.30005(7) 0.0529(6) Uani d . 1 . .
H H8A 0.4228 -0.1942 0.3141 0.063 Uiso calc R 1 . .
H H8B 0.4877 -0.0298 0.3030 0.063 Uiso calc R 1 . .
C C4 0.37288(11) 0.1944(4) 0.18780(7) 0.0480(5) Uani d . 1 . .
C C3 0.33244(12) 0.3998(4) 0.17682(7) 0.0569(6) Uani d . 1 . .
H H3 0.3155 0.5039 0.1995 0.068 Uiso calc R 1 . .
C C2 0.31662(12) 0.4537(5) 0.13280(7) 0.0612(6) Uani d . 1 . .
H H2 0.2893 0.5930 0.1258 0.073 Uiso calc R 1 . .
C C16 0.31355(12) 0.7171(5) 0.39060(7) 0.0619(6) Uani d . 1 . .
H H16 0.2822 0.8181 0.3753 0.074 Uiso calc R 1 . .
C C6 0.38144(13) 0.0964(5) 0.10979(7) 0.0649(7) Uani d . 1 . .
H H6 0.3982 -0.0070 0.0870 0.078 Uiso calc R 1 . .
C C5 0.39718(13) 0.0424(4) 0.15377(7) 0.0629(7) Uani d . 1 . .
H H5 0.4244 -0.0977 0.1605 0.075 Uiso calc R 1 . .
C C15 0.32395(14) 0.7662(5) 0.43632(8) 0.0681(7) Uani d . 1 . .
H H15 0.2995 0.8934 0.4509 0.082 Uiso calc R 1 . .
O O1W 0.28141(9) 0.4811(3) 0.28357(5) 0.0696(5) Uani d D 1 . .
H H1A 0.3792(14) 0.272(4) 0.2514(7) 0.104 Uiso d D 1 . .
H H1WA 0.2599(13) 0.621(3) 0.2800(7) 0.104 Uiso d D 1 . .
H H1WB 0.3043(12) 0.488(5) 0.3078(6) 0.104 Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O2 C8 . . 115.98(16) ?
C16 N2 C17 . . 117.87(19) ?
C7 N1 C4 . . 126.84(18) ?
C7 N1 H1A . . 115.0(19) ?
C4 N1 H1A . . 118.2(19) ?
C9 C10 C11 . . 120.1(2) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
N2 C17 C13 . . 122.04(19) ?
N2 C17 C9 . . 119.08(18) ?
C13 C17 C9 . . 118.88(19) ?
C12 C13 C14 . . 123.1(2) ?
C12 C13 C17 . . 119.5(2) ?
C14 C13 C17 . . 117.4(2) ?
O1 C7 N1 . . 124.8(2) ?
O1 C7 C8 . . 116.7(2) ?
N1 C7 C8 . . 118.50(19) ?
O2 C9 C10 . . 124.9(2) ?
O2 C9 C17 . . 115.25(18) ?
C10 C9 C17 . . 119.84(19) ?
C12 C11 C10 . . 121.5(2) ?
C12 C11 H11 . . 119.3 ?
C10 C11 H11 . . 119.3 ?
C11 C12 C13 . . 120.1(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C15 C14 C13 . . 120.3(2) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C6 C1 C2 . . 120.2(2) ?
C6 C1 Cl1 . . 119.91(18) ?
C2 C1 Cl1 . . 119.9(2) ?
O2 C8 C7 . . 113.02(17) ?
O2 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
O2 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C5 C4 C3 . . 118.5(2) ?
C5 C4 N1 . . 123.7(2) ?
C3 C4 N1 . . 117.76(19) ?
C4 C3 C2 . . 121.1(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C1 C2 C3 . . 119.6(2) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
N2 C16 C15 . . 124.3(2) ?
N2 C16 H16 . . 117.9 ?
C15 C16 H16 . . 117.9 ?
C1 C6 C5 . . 120.3(2) ?
C1 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C14 C15 C16 . . 118.2(2) ?
C14 C15 H15 . . 120.9 ?
C16 C15 H15 . . 120.9 ?
H1WA O1W H1WB . . 109.2(15) ?
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
Cl1 C1 . 1.730(2) ?
O2 C9 . 1.363(2) ?
O2 C8 . 1.425(2) ?
N2 C16 . 1.305(3) ?
N2 C17 . 1.358(2) ?
N1 C7 . 1.339(3) ?
N1 C4 . 1.411(3) ?
N1 H1A . 0.832(10) ?
C10 C9 . 1.366(3) ?
C10 C11 . 1.396(3) ?
C10 H10 . 0.9300 ?
C17 C13 . 1.412(3) ?
C17 C9 . 1.417(3) ?
C13 C12 . 1.400(3) ?
C13 C14 . 1.399(3) ?
C7 O1 . 1.212(2) ?
C7 C8 . 1.494(3) ?
C11 C12 . 1.348(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C14 C15 . 1.349(3) ?
C14 H14 . 0.9300 ?
C1 C6 . 1.365(3) ?
C1 C2 . 1.365(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C4 C5 . 1.377(3) ?
C4 C3 . 1.377(3) ?
C3 C2 . 1.379(3) ?
C3 H3 . 0.9300 ?
C2 H2 . 0.9300 ?
C16 C15 . 1.404(3) ?
C16 H16 . 0.9300 ?
C6 C5 . 1.378(3) ?
C6 H6 . 0.9300 ?
C5 H5 . 0.9300 ?
C15 H15 . 0.9300 ?
O1W H1WA . 0.854(9) ?
O1W H1WB . 0.851(9) ?
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
O1W H1WA O1W 7_665 0.854(9) 2.061(12) 2.9014(16) 168(2)
N1 H1A O2 . 0.832(10) 2.27(2) 2.702(2) 113(2)
N1 H1A O1W . 0.832(10) 2.401(19) 3.088(2) 140(2)
O1W H1WB N2 . 0.851(9) 1.988(11) 2.830(2) 170(2)
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
C16 N2 C17 C13 . . . . 0.5(3) ?
C16 N2 C17 C9 . . . . -179.92(19) ?
N2 C17 C13 C12 . . . . -179.1(2) ?
C9 C17 C13 C12 . . . . 1.3(3) ?
N2 C17 C13 C14 . . . . 0.9(3) ?
C9 C17 C13 C14 . . . . -178.67(19) ?
C4 N1 C7 O1 . . . . -4.3(4) ?
C4 N1 C7 C8 . . . . 174.31(19) ?
C8 O2 C9 C10 . . . . 6.1(3) ?
C8 O2 C9 C17 . . . . -174.00(17) ?
C11 C10 C9 O2 . . . . -179.4(2) ?
C11 C10 C9 C17 . . . . 0.8(3) ?
N2 C17 C9 O2 . . . . -1.3(3) ?
C13 C17 C9 O2 . . . . 178.33(18) ?
N2 C17 C9 C10 . . . . 178.64(19) ?
C13 C17 C9 C10 . . . . -1.8(3) ?
C9 C10 C11 C12 . . . . 0.7(4) ?
C10 C11 C12 C13 . . . . -1.2(4) ?
C14 C13 C12 C11 . . . . -179.9(2) ?
C17 C13 C12 C11 . . . . 0.1(3) ?
C12 C13 C14 C15 . . . . 178.8(2) ?
C17 C13 C14 C15 . . . . -1.2(3) ?
C9 O2 C8 C7 . . . . -175.30(17) ?
O1 C7 C8 O2 . . . . -171.25(19) ?
N1 C7 C8 O2 . . . . 10.0(3) ?
C7 N1 C4 C5 . . . . -10.4(4) ?
C7 N1 C4 C3 . . . . 171.6(2) ?
C5 C4 C3 C2 . . . . -0.2(3) ?
N1 C4 C3 C2 . . . . 177.9(2) ?
C6 C1 C2 C3 . . . . 0.1(3) ?
Cl1 C1 C2 C3 . . . . -179.29(18) ?
C4 C3 C2 C1 . . . . 0.0(3) ?
C17 N2 C16 C15 . . . . -1.7(3) ?
C2 C1 C6 C5 . . . . 0.0(4) ?
Cl1 C1 C6 C5 . . . . 179.38(19) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
N1 C4 C5 C6 . . . . -177.6(2) ?
C1 C6 C5 C4 . . . . -0.2(4) ?
C13 C14 C15 C16 . . . . 0.2(4) ?
N2 C16 C15 C14 . . . . 1.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656163
