#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520355.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520355
loop_
_publ_author_name
'Coles, Susanne L.'
'Threlfall, Terry L.'
'Hursthouse, Michael B.'
_publ_section_title
;
 N-(4-butoxyphenyl)acetamide
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1402
_journal_year                    2009
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.27
_chemical_name_systematic
;
 N-(4-butoxyphenyl)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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.691(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5164(3)
_cell_length_b                   9.8032(3)
_cell_length_c                   10.9034(2)
_cell_measurement_reflns_used    10636
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1118.54(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16589
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                2149
_reflns_number_total             2552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-1402.cif
_cod_data_source_block           2009lsh070
_cod_depositor_comments
;
Citation :
Coles (nee Huth), Susanne L. and Threlfall, Terry L. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1402)

More at:
http://ecrystals.chem.soton.ac.uk/1402/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520355
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_type_symbol
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11270(10) 0.07465(11) 1.10690(10) 0.0171(2) Uani 1 1 d . . .
C2 C 0.10277(11) 0.18948(12) 1.03174(10) 0.0196(2) Uani 1 1 d . . .
H2 H 0.0322 0.2496 1.0343 0.024 Uiso 1 1 calc R . .
C3 C 0.19609(11) 0.21682(11) 0.95240(10) 0.0198(2) Uani 1 1 d . . .
H3 H 0.1890 0.2955 0.9013 0.024 Uiso 1 1 calc R . .
C4 C 0.29920(10) 0.12903(11) 0.94821(10) 0.0175(2) Uani 1 1 d . . .
C5 C 0.30804(11) 0.01265(11) 1.02202(10) 0.0197(2) Uani 1 1 d . . .
H5 H 0.3780 -0.0482 1.0187 0.024 Uiso 1 1 calc R . .
C6 C 0.21538(11) -0.01449(11) 1.10006(10) 0.0194(2) Uani 1 1 d . . .
H6 H 0.2215 -0.0945 1.1495 0.023 Uiso 1 1 calc R . .
C7 C -0.05763(10) 0.12548(12) 1.24279(10) 0.0200(2) Uani 1 1 d . . .
C8 C -0.14581(12) 0.05724(13) 1.32481(12) 0.0280(3) Uani 1 1 d . . .
H8A H -0.1440 0.1072 1.4028 0.042 Uiso 1 1 calc R . .
H8B H -0.1177 -0.0369 1.3411 0.042 Uiso 1 1 calc R . .
H8C H -0.2331 0.0571 1.2838 0.042 Uiso 1 1 calc R . .
C9 C 0.39192(11) 0.26318(11) 0.79514(10) 0.0203(2) Uani 1 1 d . . .
H9A H 0.3879 0.3482 0.8436 0.024 Uiso 1 1 calc R . .
H9B H 0.3150 0.2584 0.7351 0.024 Uiso 1 1 calc R . .
C10 C 0.51158(11) 0.26175(12) 0.72851(10) 0.0198(2) Uani 1 1 d . . .
H10A H 0.5873 0.2609 0.7902 0.024 Uiso 1 1 calc R . .
H10B H 0.5148 0.3466 0.6796 0.024 Uiso 1 1 calc R . .
C11 C 0.51849(12) 0.13978(12) 0.64324(11) 0.0236(3) Uani 1 1 d . . .
H11A H 0.4422 0.1400 0.5823 0.028 Uiso 1 1 calc R . .
H11B H 0.5164 0.0550 0.6924 0.028 Uiso 1 1 calc R . .
C12 C 0.63795(12) 0.13905(13) 0.57481(11) 0.0256(3) Uani 1 1 d . . .
H12A H 0.6387 0.2206 0.5229 0.038 Uiso 1 1 calc R . .
H12B H 0.6379 0.0574 0.5230 0.038 Uiso 1 1 calc R . .
H12C H 0.7140 0.1387 0.6345 0.038 Uiso 1 1 calc R . .
N1 N 0.02137(9) 0.03983(10) 1.18952(9) 0.0193(2) Uani 1 1 d D . .
O1 O -0.05947(8) 0.25006(8) 1.22622(8) 0.0260(2) Uani 1 1 d . . .
O2 O 0.39746(7) 0.14650(8) 0.87542(7) 0.0210(2) Uani 1 1 d . . .
H1N H 0.0188(13) -0.0470(13) 1.2094(13) 0.028(4) Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 119.23(10) . .
C2 C1 N1 123.49(10) . .
C6 C1 N1 117.26(10) . .
C1 C2 C3 120.27(10) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C4 C3 C2 120.02(10) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
O2 C4 C3 125.16(10) . .
O2 C4 C5 115.11(10) . .
C3 C4 C5 119.72(10) . .
C6 C5 C4 120.16(10) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C1 120.57(10) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
O1 C7 N1 123.56(11) . .
O1 C7 C8 121.62(10) . .
N1 C7 C8 114.81(10) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O2 C9 C10 107.42(9) . .
O2 C9 H9A 110.2 . .
C10 C9 H9A 110.2 . .
O2 C9 H9B 110.2 . .
C10 C9 H9B 110.2 . .
H9A C9 H9B 108.5 . .
C9 C10 C11 113.14(9) . .
C9 C10 H10A 109.0 . .
C11 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
C11 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C10 C11 C12 113.26(10) . .
C10 C11 H11A 108.9 . .
C12 C11 H11A 108.9 . .
C10 C11 H11B 108.9 . .
C12 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C7 N1 C1 127.26(10) . .
C7 N1 H1N 117.4(9) . .
C1 N1 H1N 115.3(9) . .
C4 O2 C9 117.59(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3902(16) .
C1 C6 1.3968(15) .
C1 N1 1.4220(14) .
C2 C3 1.3971(16) .
C2 H2 0.9500 .
C3 C4 1.3887(16) .
C3 H3 0.9500 .
C4 O2 1.3746(13) .
C4 C5 1.3940(15) .
C5 C6 1.3816(15) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O1 1.2344(14) .
C7 N1 1.3522(14) .
C7 C8 1.5072(16) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 O2 1.4379(13) .
C9 C10 1.5143(16) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.5207(15) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.5235(16) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
N1 H1N 0.880(12) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.880(12) 2.138(13) 3.0001(13) 166.3(13) 2_547
