#------------------------------------------------------------------------------
#$Date: 2016-05-11 06:36:32 +0300 (Wed, 11 May 2016) $
#$Revision: 182864 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/32/1543279.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_1543279
loop_
_publ_author_name
'Wang, Chang-Kai'
'Zheng, Kang'
'Li, Yan-Tuan'
'Wu, Zhi-Yong'
_publ_section_title
;
 N-(5-Chloro-2-hydroxyphenyl)-N'-(3-hydroxypropyl)oxalamide
;
_journal_coeditor_code           SJ4028
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x160737
_journal_paper_doi               10.1107/S2414314616007379
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C11 H13 Cl N2 O4'
_chemical_formula_moiety         'C11 H13 Cl N2 O4'
_chemical_formula_sum            'C11 H13 Cl N2 O4'
_chemical_formula_weight         272.68
_chemical_name_systematic
;
N-(5-Chloro-2-hydroxyphenyl)-N'-(3-hydroxypropyl)ethanediamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.896(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1422(14)
_cell_length_b                   18.117(4)
_cell_length_c                   11.061(2)
_cell_measurement_reflns_used    2400
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.022
_cell_measurement_theta_min      3.541
_cell_volume                     1216.0(4)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
XP in SHELXTL  (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10616
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_min         3.541
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1042
_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
'w=1/[σ²(Fo²)+(0.0419P)²+0.2977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                1672
_reflns_number_total             2779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj4028sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1216.0(5)
_cod_database_code               1543279
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
Cl Cl1 0.54932(13) 0.33941(3) 0.39890(7) 0.0621(3) Uani d 1
O O1 0.2065(3) 0.63169(9) 0.24549(16) 0.0484(5) Uani d 1
O O2 0.7936(3) 0.50435(8) 0.08106(16) 0.0485(5) Uani d 1
O O3 0.6905(2) 0.69246(8) 0.03286(14) 0.0400(4) Uani d 1
O O4 1.4561(3) 0.80399(10) -0.10518(19) 0.0523(5) Uani d 1
N N1 0.5547(3) 0.58139(10) 0.15803(17) 0.0334(5) Uani d 1
N N2 0.8959(3) 0.61585(10) -0.06633(18) 0.0356(5) Uani d 1
C C1 0.4604(3) 0.53575(11) 0.23849(19) 0.0312(5) Uani d 1
C C2 0.2779(4) 0.56333(12) 0.2848(2) 0.0356(5) Uani d 1
C C3 0.1802(4) 0.52106(14) 0.3647(2) 0.0449(6) Uani d 1
C C4 0.2617(4) 0.45182(13) 0.4005(2) 0.0450(6) Uani d 1
C C5 0.4420(4) 0.42605(12) 0.3552(2) 0.0390(6) Uani d 1
C C6 0.5429(4) 0.46656(12) 0.2747(2) 0.0345(5) Uani d 1
C C7 0.7077(3) 0.56439(11) 0.0884(2) 0.0310(5) Uani d 1
C C8 0.7663(3) 0.63118(11) 0.0148(2) 0.0308(5) Uani d 1
C C9 0.9727(4) 0.67265(14) -0.1426(2) 0.0385(6) Uani d 1
C C10 1.1919(4) 0.70438(13) -0.0862(2) 0.0363(6) Uani d 1
C C11 1.2472(4) 0.77284(13) -0.1527(2) 0.0398(6) Uani d 1
H H1 0.507(4) 0.6260(14) 0.150(2) 0.049(7) Uiso d 1
H H1A 0.122(4) 0.6487(14) 0.288(2) 0.061(9) Uiso d 1
H H2 0.946(4) 0.5705(14) -0.068(2) 0.052(8) Uiso d 1
H H3 0.060(4) 0.5401(13) 0.394(2) 0.048(7) Uiso d 1
H H4 0.191(4) 0.4237(12) 0.453(2) 0.044(7) Uiso d 1
H H4A 1.527(5) 0.7724(14) -0.065(3) 0.086(12) Uiso d 1
H H6 0.663(4) 0.4498(12) 0.2439(19) 0.038(6) Uiso d 1
H H9A 0.863(4) 0.7103(13) -0.158(2) 0.048(7) Uiso d 1
H H9B 0.985(4) 0.6512(13) -0.223(2) 0.051(7) Uiso d 1
H H10A 1.300(4) 0.6690(13) -0.089(2) 0.049(7) Uiso d 1
H H10B 1.191(4) 0.7173(12) 0.001(2) 0.047(7) Uiso d 1
H H11A 1.134(4) 0.8107(13) -0.142(2) 0.051(7) Uiso d 1
H H11B 1.244(4) 0.7627(13) -0.239(2) 0.055(8) Uiso 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
C2 O1 H1A 111.1(19)
C11 O4 H4A 107(2)
C7 N1 C1 128.59(18)
C7 N1 H1 114.1(16)
C1 N1 H1 117.2(16)
C8 N2 C9 122.0(2)
C8 N2 H2 117.3(16)
C9 N2 H2 120.4(16)
C6 C1 C2 119.7(2)
C6 C1 N1 123.15(19)
C2 C1 N1 117.09(18)
O1 C2 C3 124.1(2)
O1 C2 C1 116.49(19)
C3 C2 C1 119.4(2)
C2 C3 C4 120.9(2)
C2 C3 H3 118.0(15)
C4 C3 H3 121.1(15)
C5 C4 C3 118.8(2)
C5 C4 H4 121.6(14)
C3 C4 H4 119.6(14)
C4 C5 C6 121.9(2)
C4 C5 Cl1 119.99(18)
C6 C5 Cl1 118.14(17)
C5 C6 C1 119.2(2)
C5 C6 H6 122.5(14)
C1 C6 H6 118.3(14)
O2 C7 N1 126.43(19)
O2 C7 C8 122.01(18)
N1 C7 C8 111.56(17)
O3 C8 N2 125.7(2)
O3 C8 C7 119.94(18)
N2 C8 C7 114.32(18)
N2 C9 C10 112.3(2)
N2 C9 H9A 109.1(14)
C10 C9 H9A 111.4(14)
N2 C9 H9B 108.7(14)
C10 C9 H9B 109.7(14)
H9A C9 H9B 106(2)
C11 C10 C9 111.5(2)
C11 C10 H10A 109.9(14)
C9 C10 H10A 108.7(14)
C11 C10 H10B 108.4(13)
C9 C10 H10B 110.5(13)
H10A C10 H10B 108(2)
O4 C11 C10 113.8(2)
O4 C11 H11A 106.9(13)
C10 C11 H11A 107.2(13)
O4 C11 H11B 108.6(14)
C10 C11 H11B 110.7(15)
H11A C11 H11B 109.4(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.742(2)
O1 C2 1.362(3)
O1 H1A 0.813(17)
O2 C7 1.217(2)
O3 C8 1.232(2)
O4 C11 1.426(3)
O4 H4A 0.812(17)
N1 C7 1.340(3)
N1 C1 1.404(3)
N1 H1 0.86(2)
N2 C8 1.317(3)
N2 C9 1.454(3)
N2 H2 0.88(2)
C1 C6 1.388(3)
C1 C2 1.395(3)
C2 C3 1.375(3)
C3 C4 1.385(3)
C3 H3 0.92(2)
C4 C5 1.366(3)
C4 H4 0.93(2)
C5 C6 1.374(3)
C6 H6 0.91(2)
C7 C8 1.532(3)
C9 C10 1.507(3)
C9 H9A 0.96(2)
C9 H9B 0.98(2)
C10 C11 1.507(3)
C10 H10A 0.93(2)
C10 H10B 0.99(2)
C11 H11A 1.00(2)
C11 H11B 0.97(2)
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
O1 H1A O4 4_476 0.813(17) 1.881(17) 2.690(2) 173(3)
O4 H4A O3 1_655 0.812(17) 1.983(18) 2.794(2) 178(3)
N2 H2 O2 3_765 0.88(2) 2.12(3) 2.916(2) 150(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
C7 N1 C1 C6 11.8(4)
C7 N1 C1 C2 -169.5(2)
C6 C1 C2 O1 179.8(2)
N1 C1 C2 O1 1.1(3)
C6 C1 C2 C3 -0.9(3)
N1 C1 C2 C3 -179.5(2)
O1 C2 C3 C4 179.9(2)
C1 C2 C3 C4 0.5(4)
C2 C3 C4 C5 0.2(4)
C3 C4 C5 C6 -0.6(4)
C3 C4 C5 Cl1 179.7(2)
C4 C5 C6 C1 0.3(4)
Cl1 C5 C6 C1 179.97(18)
C2 C1 C6 C5 0.5(3)
N1 C1 C6 C5 179.1(2)
C1 N1 C7 O2 0.9(4)
C1 N1 C7 C8 -179.4(2)
C9 N2 C8 O3 2.5(4)
C9 N2 C8 C7 -178.6(2)
O2 C7 C8 O3 -173.5(2)
N1 C7 C8 O3 6.7(3)
O2 C7 C8 N2 7.5(3)
N1 C7 C8 N2 -172.22(19)
C8 N2 C9 C10 92.4(3)
N2 C9 C10 C11 -168.6(2)
C9 C10 C11 O4 -178.3(2)

_cod_database_fobs_code 1543279
