##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     CRYSTALS_ver_14.06
_journal_date_recd_electronic     2010-12-29
_journal_date_accepted     2011-01-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      3
_journal_page_first     o612
_journal_page_last     o612
_journal_paper_category     QO
_journal_coeditor_code     KP2300
_publ_contact_author_name     'SIDIK BIN SILONG'
_publ_contact_author_address
;
Department of Chemistry, Faculty of Science,
Universiti Putra Malaysia,
43400 UPM Serdang, Selangor,
Malaysia
;
_publ_contact_author_email     sidik@science.upm.edu.my
_publ_contact_author_fax     '+603-89435380 '
_publ_contact_author_phone     '+603-89466806 '
_publ_section_title
;
4-Hexyloxybenzamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kwong, Huey Chong' .
;
Department of Chemistry,
Faculty of Science,
Universiti Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Mohamad Zaki Ab. Rahman' .
;
Department of Chemistry,
Faculty of Science,
Universiti Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Mohamed Tahir, Mohamed Ibrahim' .
;
Department of Chemistry,
Faculty of Science,
Universiti Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Silong, Sidik' .
;
Department of Chemistry,
Faculty of Science,
Universiti Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
data_I
_chemical_name_systematic
;
4-Hexyloxybenzamide
;
_chemical_formula_moiety     'C13 H19 N1 O2'
_chemical_formula_sum     'C13 H19 N1 O2'
_chemical_formula_iupac     'C13 H19 N1 O2'
_chemical_formula_weight     221.30
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn '
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x+1/2,y+1/2,-z+1/2'
    'x+1/2,-y+1/2,z+1/2'
_cell_length_a     12.5507(2)
_cell_length_b     5.16441(9)
_cell_length_c     18.9322(3)
_cell_angle_alpha     90
_cell_angle_beta     91.4702(16)
_cell_angle_gamma     90
_cell_volume     1226.72(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8720
_cell_measurement_theta_min     3.5198
_cell_measurement_theta_max     70.8427
_cell_measurement_temperature     150
_exptl_crystal_description     'needle-like'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.314
_exptl_crystal_size_mid     0.075
_exptl_crystal_size_min     0.046
_exptl_crystal_density_diffrn     1.198
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.640
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO: Oxford Diffraction, 2006)
;
_exptl_absorpt_correction_T_min     0.89422
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     150
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'sealed x-ray tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Diffraction Gemini E'
_diffrn_measurement_device     'Area'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     13258
_diffrn_reflns_av_R_equivalents     0.018
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     4.177
_diffrn_reflns_theta_max     70.980
_diffrn_reflns_theta_full     69.560
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
For this compound, 13258 reflections were measured and collected during
the refinement. However after merging the symmetry equivalent
reflections, there were only 2355 independent reflections. Further 254
more reflections were filtered, as sigma cutoff was set at 3.0 and
(sin theta x 2)set to >0.01  (to eliminate reflection measured near
the vicinity of beam stop) therefore reduced the number of reflection to
2101 which were used in the Refinement.
;
_reflns_number_total     2355
_reflns_number_gt     2165
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0394
_refine_ls_R_factor_gt     0.0369
_refine_ls_wR_factor_all     0.0983
_refine_ls_wR_factor_gt     0.0960
_refine_ls_wR_factor_ref     0.0947
_refine_ls_goodness_of_fit_ref     1.0093
_refine_ls_number_reflns     2101
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + (0.05P)² + 0.41P], where P=[max(Fo²,0) + 2Fc²]/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.0002608
_refine_ls_shift/su_mean     0.0000241
_refine_diff_density_max     0.18
_refine_diff_density_min     -0.18
_refine_ls_extinction_method     'None'
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0181 0.0091 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0311 0.0180 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0492 0.0322 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'Mercury (Macrae et al., 2006)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.50007(7) 0.75339(18) 0.27977(5) 0.0339 Uani 1.0000 . .
    C C2 0.40797(9) 0.7236(2) 0.31525(6) 0.0276 Uani 1.0000 . .
    C C3 0.40594(10) 0.5166(2) 0.36254(7) 0.0327 Uani 1.0000 . .
    C C4 0.31610(10) 0.4686(2) 0.40089(6) 0.0302 Uani 1.0000 . .
    C C5 0.22742(9) 0.6304(2) 0.39492(6) 0.0258 Uani 1.0000 . .
    C C6 0.23026(10) 0.8374(2) 0.34797(6) 0.0283 Uani 1.0000 . .
    C C7 0.31893(10) 0.8824(2) 0.30718(6) 0.0292 Uani 1.0000 . .
    C C8 0.13215(9) 0.5718(2) 0.43773(6) 0.0265 Uani 1.0000 . .
    O O9 0.11152(7) 0.34604(16) 0.45547(5) 0.0322 Uani 1.0000 . .
    N N10 0.07033(9) 0.7708(2) 0.45501(6) 0.0326 Uani 1.0000 . .
    C C11 0.50247(10) 0.9496(3) 0.22591(7) 0.0334 Uani 1.0000 . .
    C C12 0.61157(10) 0.9498(2) 0.19414(7) 0.0337 Uani 1.0000 . .
    C C13 0.64375(10) 0.6928(2) 0.16146(7) 0.0321 Uani 1.0000 . .
    C C14 0.74928(10) 0.7091(2) 0.12345(7) 0.0314 Uani 1.0000 . .
    C C15 0.78664(10) 0.4500(3) 0.09497(7) 0.0339 Uani 1.0000 . .
    C C16 0.89010(11) 0.4699(3) 0.05528(7) 0.0392 Uani 1.0000 . .
    H H31 0.4688 0.4087 0.3672 0.0424 Uiso 1.0000 . .
    H H41 0.3139 0.3171 0.4318 0.0397 Uiso 1.0000 . .
    H H61 0.1691 0.9533 0.3429 0.0368 Uiso 1.0000 . .
    H H71 0.3177 1.0309 0.2744 0.0385 Uiso 1.0000 . .
    H H112 0.4882 1.1252 0.2475 0.0433 Uiso 1.0000 . .
    H H111 0.4461 0.9082 0.1885 0.0424 Uiso 1.0000 . .
    H H122 0.6652 1.0029 0.2319 0.0438 Uiso 1.0000 . .
    H H121 0.6111 1.0874 0.1576 0.0426 Uiso 1.0000 . .
    H H131 0.6479 0.5555 0.1986 0.0402 Uiso 1.0000 . .
    H H132 0.5859 0.6413 0.1263 0.0417 Uiso 1.0000 . .
    H H141 0.8049 0.7782 0.1575 0.0417 Uiso 1.0000 . .
    H H142 0.7433 0.8391 0.0847 0.0407 Uiso 1.0000 . .
    H H151 0.7949 0.3232 0.1343 0.0435 Uiso 1.0000 . .
    H H152 0.7299 0.3781 0.0628 0.0445 Uiso 1.0000 . .
    H H162 0.9124 0.2983 0.0389 0.0627 Uiso 1.0000 . .
    H H163 0.9472 0.5385 0.0870 0.0619 Uiso 1.0000 . .
    H H161 0.8823 0.5875 0.0142 0.0630 Uiso 1.0000 . .
    H H101 0.0938 0.9339 0.4498 0.0433 Uiso 1.0000 . .
    H H102 0.0124 0.7437 0.4808 0.0432 Uiso 1.0000 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0292(4) 0.0377(5) 0.0350(5) 0.0032(4) 0.0051(4) 0.0078(4)
    C2 0.0281(6) 0.0268(6) 0.0279(6) -0.0015(5) 0.0011(4) -0.0021(5)
    C3 0.0319(6) 0.0296(6) 0.0365(7) 0.0059(5) 0.0000(5) 0.0042(5)
    C4 0.0367(7) 0.0238(6) 0.0300(6) 0.0010(5) 0.0007(5) 0.0046(5)
    C5 0.0312(6) 0.0199(5) 0.0264(5) -0.0024(4) 0.0004(4) -0.0026(4)
    C6 0.0317(6) 0.0209(6) 0.0325(6) 0.0024(5) 0.0019(5) 0.0006(5)
    C7 0.0346(6) 0.0220(6) 0.0311(6) -0.0002(5) 0.0029(5) 0.0039(5)
    C8 0.0331(6) 0.0216(6) 0.0248(5) -0.0019(5) 0.0001(5) -0.0006(4)
    O9 0.0390(5) 0.0201(4) 0.0378(5) -0.0009(3) 0.0095(4) 0.0028(3)
    N10 0.0382(6) 0.0204(5) 0.0399(6) -0.0006(4) 0.0136(5) 0.0011(4)
    C11 0.0356(7) 0.0278(6) 0.0373(7) 0.0011(5) 0.0070(5) 0.0042(5)
    C12 0.0353(7) 0.0279(6) 0.0382(7) -0.0037(5) 0.0071(5) 0.0001(5)
    C13 0.0316(6) 0.0277(6) 0.0370(7) -0.0031(5) 0.0030(5) -0.0013(5)
    C14 0.0335(6) 0.0271(6) 0.0335(6) -0.0027(5) 0.0024(5) -0.0002(5)
    C15 0.0335(7) 0.0292(7) 0.0391(7) -0.0018(5) 0.0013(5) -0.0039(5)
    C16 0.0368(7) 0.0393(8) 0.0415(7) 0.0014(6) 0.0031(6) -0.0071(6)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C2 . . 1.3605(14) no
    O1 C11 . . 1.4384(15) no
    C2 C3 . . 1.3954(17) no
    C2 C7 . . 1.3915(17) no
    C3 C4 . . 1.3792(17) no
    C3 H31 . . 0.968 no
    C4 C5 . . 1.3943(17) no
    C4 H41 . . 0.978 no
    C5 C6 . . 1.3912(16) no
    C5 C8 . . 1.4926(16) no
    C6 C7 . . 1.3904(17) no
    C6 H61 . . 0.976 no
    C7 H71 . . 0.986 no
    C8 O9 . . 1.2423(14) no
    C8 N10 . . 1.3338(15) no
    N10 H101 . . 0.898 no
    N10 H102 . . 0.898 no
    C11 C12 . . 1.5096(17) no
    C11 H112 . . 1.013 no
    C11 H111 . . 1.011 no
    C12 C13 . . 1.5233(17) no
    C12 H122 . . 1.007 no
    C12 H121 . . 0.992 no
    C13 C14 . . 1.5258(17) no
    C13 H131 . . 0.998 no
    C13 H132 . . 1.007 no
    C14 C15 . . 1.5216(17) no
    C14 H141 . . 1.003 no
    C14 H142 . . 0.996 no
    C15 C16 . . 1.5203(18) no
    C15 H151 . . 0.995 no
    C15 H152 . . 0.997 no
    C16 H162 . . 0.982 no
    C16 H163 . . 0.989 no
    C16 H161 . . 0.990 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 C11 . . . 117.58(9) ?
    O1 C2 C3 . . . 115.66(11) ?
    O1 C2 C7 . . . 124.71(11) no
    C3 C2 C7 . . . 119.63(11) ?
    C2 C3 C4 . . . 120.28(11) ?
    C2 C3 H31 . . . 118.1 no
    C4 C3 H31 . . . 121.6 no
    C3 C4 C5 . . . 120.75(11) ?
    C3 C4 H41 . . . 119.7 no
    C5 C4 H41 . . . 119.5 no
    C4 C5 C6 . . . 118.62(11) ?
    C4 C5 C8 . . . 118.89(10) ?
    C6 C5 C8 . . . 122.47(11) ?
    C5 C6 C7 . . . 121.16(11) ?
    C5 C6 H61 . . . 120.1 no
    C7 C6 H61 . . . 118.8 no
    C2 C7 C6 . . . 119.50(11) no
    C2 C7 H71 . . . 121.8 no
    C6 C7 H71 . . . 118.6 no
    C5 C8 O9 . . . 120.85(10) no
    C5 C8 N10 . . . 117.12(10) no
    O9 C8 N10 . . . 122.03(11) no
    C8 N10 H101 . . . 120.1 no
    C8 N10 H102 . . . 119.9 no
    H101 N10 H102 . . . 118.5 no
    O1 C11 C12 . . . 108.58(10) no
    O1 C11 H112 . . . 109.7 no
    C12 C11 H112 . . . 109.4 no
    O1 C11 H111 . . . 108.7 no
    C12 C11 H111 . . . 110.3 no
    H112 C11 H111 . . . 110.1 no
    C11 C12 C13 . . . 114.45(10) no
    C11 C12 H122 . . . 108.3 no
    C13 C12 H122 . . . 110.2 no
    C11 C12 H121 . . . 106.8 no
    C13 C12 H121 . . . 109.7 no
    H122 C12 H121 . . . 106.9 no
    C12 C13 C14 . . . 112.69(10) no
    C12 C13 H131 . . . 110.0 no
    C14 C13 H131 . . . 110.0 no
    C12 C13 H132 . . . 107.7 no
    C14 C13 H132 . . . 108.8 no
    H131 C13 H132 . . . 107.5 no
    C13 C14 C15 . . . 113.43(10) no
    C13 C14 H141 . . . 108.4 no
    C15 C14 H141 . . . 109.0 no
    C13 C14 H142 . . . 109.6 no
    C15 C14 H142 . . . 110.5 no
    H141 C14 H142 . . . 105.7 no
    C14 C15 C16 . . . 112.97(11) no
    C14 C15 H151 . . . 109.9 no
    C16 C15 H151 . . . 109.9 no
    C14 C15 H152 . . . 108.8 no
    C16 C15 H152 . . . 109.2 no
    H151 C15 H152 . . . 105.8 no
    C15 C16 H162 . . . 110.4 no
    C15 C16 H163 . . . 109.8 no
    H162 C16 H163 . . . 107.9 no
    C15 C16 H161 . . . 111.2 no
    H162 C16 H161 . . . 109.2 no
    H163 C16 H161 . . . 108.3 no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    N10 H101 O9 . . 1_565 0.90 2.14 3.0153(18) 164 yes
    N10 H102 O9 . . 2_566 0.90 2.04 2.9401(18) 174 yes
