#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229050.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_2229050
loop_
_publ_author_name
'Yang, Ming-Ming'
'Li, Fang-Shi'
'Lu, Qi-Sheng'
'Wang, Hao-Wei'
'Xie, Qing'
_publ_section_title
;
 N-(4-Butanoyl-3-hydroxyphenyl)butanamide
;
_journal_coeditor_code           GK2334
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o441
_journal_paper_doi               10.1107/S1600536811001279
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H19 N O3'
_chemical_formula_moiety         'C14 H19 N O3'
_chemical_formula_sum            'C14 H19 N O3'
_chemical_formula_weight         249.30
_chemical_melting_point          381
_chemical_name_systematic
;
N-(4-Butanoyl-3-hydroxyphenyl)butanamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2870(13)
_cell_length_b                   10.008(2)
_cell_length_c                   21.680(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1351.0(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2684
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.182
_refine_ls_extinction_coef       0.045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0496
_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)+(0.1000P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                1732
_reflns_number_total             2448
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2334.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229050
_cod_database_fobs_code          2229050
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.1152(3) 0.62012(16) 0.25206(8) 0.0443(5) Uani d . 1 . .
H H1N 0.1438 0.7034 0.2480 0.053 Uiso calc R 1 . .
O O1 0.2269(3) 0.41334(15) 0.22806(8) 0.0653(5) Uani d . 1 . .
O O2 -0.3406(3) 0.31968(14) 0.34457(8) 0.0624(5) Uani d . 1 . .
H H2A -0.4387 0.3191 0.3659 0.094 Uiso calc R 1 . .
O O3 -0.6164(3) 0.41920(16) 0.40749(9) 0.0686(5) Uani d . 1 . .
C C1 0.1729(6) 0.5577(3) 0.07966(14) 0.0959(10) Uani d . 1 . .
H H1A 0.1779 0.5148 0.0403 0.144 Uiso calc R 1 . .
H H1B 0.1475 0.6515 0.0732 0.144 Uiso calc R 1 . .
H H1C 0.0590 0.5196 0.0992 0.144 Uiso calc R 1 . .
C C2 0.3834(5) 0.5374(2) 0.12083(11) 0.0668(7) Uani d . 1 . .
H H2B 0.4978 0.5753 0.1006 0.080 Uiso calc R 1 . .
H H2C 0.4104 0.4423 0.1259 0.080 Uiso calc R 1 . .
C C3 0.3882(4) 0.6008(2) 0.18464(11) 0.0547(6) Uani d . 1 . .
H H3A 0.5332 0.5959 0.2067 0.066 Uiso calc R 1 . .
H H3B 0.3502 0.6945 0.1795 0.066 Uiso calc R 1 . .
C C4 0.2373(3) 0.5346(2) 0.22330(10) 0.0445(5) Uani d . 1 . .
C C5 -0.0507(3) 0.59311(17) 0.28740(9) 0.0398(5) Uani d . 1 . .
C C6 -0.1165(3) 0.46492(18) 0.29964(10) 0.0442(5) Uani d . 1 . .
H H6A -0.0497 0.3914 0.2844 0.053 Uiso calc R 1 . .
C C7 -0.2832(3) 0.44685(19) 0.33483(9) 0.0444(5) Uani d . 1 . .
C C8 -0.3858(3) 0.55602(19) 0.35889(9) 0.0425(5) Uani d . 1 . .
C C9 -0.3162(3) 0.6842(2) 0.34437(9) 0.0453(5) Uani d . 1 . .
H H9A -0.3830 0.7585 0.3589 0.054 Uiso calc R 1 . .
C C10 -0.1537(3) 0.70308(19) 0.30956(9) 0.0442(5) Uani d . 1 . .
H H10A -0.1116 0.7892 0.3006 0.053 Uiso calc R 1 . .
C C11 -0.5560(3) 0.5341(2) 0.39762(10) 0.0490(5) Uani d . 1 . .
C C12 -0.6540(3) 0.6497(2) 0.42757(10) 0.0534(6) Uani d . 1 . .
H H12A -0.7122 0.7119 0.3953 0.064 Uiso calc R 1 . .
H H12B -0.5417 0.6957 0.4547 0.064 Uiso calc R 1 . .
C C13 -0.8299(4) 0.6116(3) 0.46512(10) 0.0580(6) Uani d . 1 . .
H H13A -0.7728 0.5484 0.4971 0.070 Uiso calc R 1 . .
H H13B -0.9440 0.5673 0.4380 0.070 Uiso calc R 1 . .
C C14 -0.9232(5) 0.7300(3) 0.49570(12) 0.0794(8) Uani d . 1 . .
H H14A -1.0325 0.6996 0.5192 0.119 Uiso calc R 1 . .
H H14B -0.9846 0.7916 0.4642 0.119 Uiso calc R 1 . .
H H14C -0.8115 0.7738 0.5231 0.119 Uiso calc R 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'
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
C4 N1 C5 . . 129.76(17) ?
C4 N1 H1N . . 115.1 ?
C5 N1 H1N . . 115.1 ?
C7 O2 H2A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C1 C2 C3 . . 112.9(2) ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
C1 C2 H2C . . 109.0 ?
C3 C2 H2C . . 109.0 ?
H2B C2 H2C . . 107.8 ?
C4 C3 C2 . . 112.88(19) ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3B . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
O1 C4 N1 . . 123.21(19) ?
O1 C4 C3 . . 122.04(19) ?
N1 C4 C3 . . 114.76(18) ?
C6 C5 C10 . . 119.95(18) ?
C6 C5 N1 . . 123.20(17) ?
C10 C5 N1 . . 116.84(16) ?
C5 C6 C7 . . 119.58(18) ?
C5 C6 H6A . . 120.2 ?
C7 C6 H6A . . 120.2 ?
O2 C7 C6 . . 116.59(17) ?
O2 C7 C8 . . 121.95(19) ?
C6 C7 C8 . . 121.46(18) ?
C9 C8 C7 . . 116.97(18) ?
C9 C8 C11 . . 122.65(18) ?
C7 C8 C11 . . 120.38(18) ?
C10 C9 C8 . . 122.01(18) ?
C10 C9 H9A . . 119.0 ?
C8 C9 H9A . . 119.0 ?
C9 C10 C5 . . 120.00(18) ?
C9 C10 H10A . . 120.0 ?
C5 C10 H10A . . 120.0 ?
O3 C11 C8 . . 120.2(2) ?
O3 C11 C12 . . 119.15(19) ?
C8 C11 C12 . . 120.61(18) ?
C11 C12 C13 . . 114.48(19) ?
C11 C12 H12A . . 108.6 ?
C13 C12 H12A . . 108.6 ?
C11 C12 H12B . . 108.6 ?
C13 C12 H12B . . 108.6 ?
H12A C12 H12B . . 107.6 ?
C12 C13 C14 . . 113.3(2) ?
C12 C13 H13A . . 108.9 ?
C14 C13 H13A . . 108.9 ?
C12 C13 H13B . . 108.9 ?
C14 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
N1 C4 . 1.357(3) ?
N1 C5 . 1.403(2) ?
N1 H1N . 0.8600 ?
O1 C4 . 1.221(2) ?
O2 C7 . 1.348(2) ?
O2 H2A . 0.8200 ?
O3 C11 . 1.239(3) ?
C1 C2 . 1.504(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.519(3) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 C4 . 1.504(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C5 C6 . 1.385(2) ?
C5 C10 . 1.396(3) ?
C6 C7 . 1.390(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.406(3) ?
C8 C9 . 1.405(3) ?
C8 C11 . 1.466(3) ?
C9 C10 . 1.365(3) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.500(3) ?
C12 C13 . 1.510(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.515(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 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
N1 H1N O1 2_555 0.86 2.29 3.109(2) 160 yes
O2 H2A O3 . 0.82 1.83 2.552(3) 146 yes
C6 H6A O1 . 0.93 2.27 2.875(3) 122 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . 67.0(3) ?
C5 N1 C4 O1 . . . . -5.1(3) ?
C5 N1 C4 C3 . . . . 174.86(19) ?
C2 C3 C4 O1 . . . . 46.3(3) ?
C2 C3 C4 N1 . . . . -133.7(2) ?
C4 N1 C5 C6 . . . . 1.0(3) ?
C4 N1 C5 C10 . . . . -177.72(19) ?
C10 C5 C6 C7 . . . . -1.0(3) ?
N1 C5 C6 C7 . . . . -179.65(17) ?
C5 C6 C7 O2 . . . . 179.43(17) ?
C5 C6 C7 C8 . . . . -0.6(3) ?
O2 C7 C8 C9 . . . . -178.34(17) ?
C6 C7 C8 C9 . . . . 1.7(3) ?
O2 C7 C8 C11 . . . . 2.1(3) ?
C6 C7 C8 C11 . . . . -177.91(18) ?
C7 C8 C9 C10 . . . . -1.3(3) ?
C11 C8 C9 C10 . . . . 178.29(19) ?
C8 C9 C10 C5 . . . . -0.2(3) ?
C6 C5 C10 C9 . . . . 1.4(3) ?
N1 C5 C10 C9 . . . . -179.87(17) ?
C9 C8 C11 O3 . . . . 177.71(19) ?
C7 C8 C11 O3 . . . . -2.7(3) ?
C9 C8 C11 C12 . . . . -4.4(3) ?
C7 C8 C11 C12 . . . . 175.14(18) ?
O3 C11 C12 C13 . . . . -3.1(3) ?
C8 C11 C12 C13 . . . . 179.01(18) ?
C11 C12 C13 C14 . . . . 179.02(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9314639
