#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/91/2219111.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_2219111
loop_
_publ_author_name
'Li, Zhu-Bo'
'Zuo, Hua'
'Dong, Wen-Liang'
'He, Xiao-Yan'
'Chen, Zhang-Bao'
_publ_section_title
;
 N-Benzyl-2-(2-chloro-4-methylphenoxy)acetamide
;
_journal_coeditor_code           NC2110
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1609
_journal_paper_doi               10.1107/S1600536808022526
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H16 Cl N O2'
_chemical_formula_moiety         'C16 H16 Cl N O2'
_chemical_formula_sum            'C16 H16 Cl N O2'
_chemical_formula_weight         289.75
_chemical_name_systematic
;
N-Benzyl-2-(2-chloro-4-methylphenoxy)acetamide
;
_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                   11.9900(18)
_cell_length_b                   9.2986(14)
_cell_length_c                   25.868(4)
_cell_measurement_reflns_used    2043
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.89
_cell_measurement_theta_min      2.88
_cell_volume                     2884.0(8)
_computing_cell_refinement       'APEX2 [or SMART?] (Bruker, 2005)'
_computing_data_collection       'APEX2 [or SMART?] (Bruker, 2005)'
_computing_data_reduction        'APEX2 [or SMART?] (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15831
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0455
_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)+(0.06P)²+0.774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                1964
_reflns_number_total             3286
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2110.cif
_cod_data_source_block           I
_cod_original_cell_volume        2884.1(7)
_cod_database_code               2219111
_cod_database_fobs_code          2219111
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
N N 0.25818(17) 0.4733(2) 0.38688(7) 0.0475(5) Uani d . 1
H H 0.2699(18) 0.557(3) 0.3929(9) 0.049(7) Uiso d . 1
Cl Cl1 0.03007(5) 0.17559(7) 0.57574(3) 0.0657(2) Uani d . 1
O O1 0.12962(13) 0.38711(16) 0.50994(6) 0.0518(4) Uani d . 1
O O2 0.19800(14) 0.26379(16) 0.42037(6) 0.0557(4) Uani d . 1
C C1 0.17217(18) 0.2116(2) 0.57204(8) 0.0449(5) Uani d . 1
C C2 0.24535(19) 0.1359(2) 0.60276(8) 0.0479(5) Uani d . 1
H H2 0.2178 0.0675 0.6257 0.057 Uiso calc R 1
C C3 0.35942(19) 0.1599(2) 0.60016(9) 0.0484(5) Uani d . 1
C C4 0.4390(2) 0.0750(3) 0.63326(10) 0.0669(7) Uani d . 1
H H4A 0.5140 0.1053 0.6263 0.100 Uiso calc R 1
H H4B 0.4315 -0.0255 0.6255 0.100 Uiso calc R 1
H H4C 0.4221 0.0911 0.6691 0.100 Uiso calc R 1
C C5 0.3965(2) 0.2623(3) 0.56529(9) 0.0518(6) Uani d . 1
H H5 0.4726 0.2803 0.5626 0.062 Uiso calc R 1
C C6 0.32366(19) 0.3384(2) 0.53445(9) 0.0498(6) Uani d . 1
H H6 0.3514 0.4062 0.5113 0.060 Uiso calc R 1
C C7 0.20977(18) 0.3153(2) 0.53747(8) 0.0431(5) Uani d . 1
C C8 0.1658(2) 0.4792(2) 0.46959(8) 0.0510(6) Uani d . 1
H H8A 0.2239 0.5422 0.4825 0.061 Uiso calc R 1
H H8B 0.1038 0.5387 0.4584 0.061 Uiso calc R 1
C C9 0.21020(18) 0.3948(2) 0.42362(8) 0.0428(5) Uani d . 1
C C10 0.2954(2) 0.4080(2) 0.33864(8) 0.0510(6) Uani d . 1
H H10A 0.2365 0.3473 0.3250 0.061 Uiso calc R 1
H H10B 0.3597 0.3477 0.3454 0.061 Uiso calc R 1
C C11 0.32561(18) 0.5196(2) 0.29900(8) 0.0441(5) Uani d . 1
C C12 0.2495(2) 0.5609(2) 0.26193(9) 0.0547(6) Uani d . 1
H H12 0.1787 0.5201 0.2619 0.066 Uiso calc R 1
C C13 0.2765(2) 0.6617(3) 0.22488(10) 0.0653(7) Uani d . 1
H H13 0.2241 0.6880 0.2001 0.078 Uiso calc R 1
C C14 0.3801(2) 0.7230(3) 0.22441(10) 0.0655(7) Uani d . 1
H H14 0.3985 0.7901 0.1991 0.079 Uiso calc R 1
C C15 0.4562(2) 0.6855(3) 0.26101(12) 0.0686(7) Uani d . 1
H H15 0.5263 0.7282 0.2611 0.082 Uiso calc R 1
C C16 0.4294(2) 0.5832(3) 0.29846(10) 0.0608(7) Uani d . 1
H H16 0.4820 0.5577 0.3232 0.073 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'
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
C9 N C10 121.07(19)
C9 N H 117.9(16)
C10 N H 120.9(16)
C7 O1 C8 117.56(17)
C2 C1 C7 121.3(2)
C2 C1 Cl1 119.61(17)
C7 C1 Cl1 119.12(17)
C1 C2 C3 121.2(2)
C1 C2 H2 119.4
C3 C2 H2 119.4
C2 C3 C5 117.3(2)
C2 C3 C4 120.9(2)
C5 C3 C4 121.8(2)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 C3 121.8(2)
C6 C5 H5 119.1
C3 C5 H5 119.1
C5 C6 C7 120.8(2)
C5 C6 H6 119.6
C7 C6 H6 119.6
O1 C7 C6 125.9(2)
O1 C7 C1 116.42(19)
C6 C7 C1 117.6(2)
O1 C8 C9 111.79(17)
O1 C8 H8A 109.3
C9 C8 H8A 109.3
O1 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 107.9
O2 C9 N 123.1(2)
O2 C9 C8 121.51(19)
N C9 C8 115.30(18)
N C10 C11 111.74(17)
N C10 H10A 109.3
C11 C10 H10A 109.3
N C10 H10B 109.3
C11 C10 H10B 109.3
H10A C10 H10B 107.9
C16 C11 C12 118.1(2)
C16 C11 C10 121.4(2)
C12 C11 C10 120.5(2)
C11 C12 C13 121.1(2)
C11 C12 H12 119.4
C13 C12 H12 119.4
C14 C13 C12 120.2(3)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 119.8(2)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C16 120.2(2)
C14 C15 H15 119.9
C16 C15 H15 119.9
C11 C16 C15 120.5(2)
C11 C16 H16 119.8
C15 C16 H16 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C9 1.329(3)
N C10 1.458(3)
N H 0.80(2)
Cl1 C1 1.739(2)
O1 C7 1.370(3)
O1 C8 1.418(3)
O2 C9 1.230(2)
C1 C2 1.377(3)
C1 C7 1.390(3)
C2 C3 1.387(3)
C2 H2 0.9300
C3 C5 1.385(3)
C3 C4 1.505(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C6 1.378(3)
C5 H5 0.9300
C6 C7 1.385(3)
C6 H6 0.9300
C8 C9 1.521(3)
C8 H8A 0.9700
C8 H8B 0.9700
C10 C11 1.503(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C16 1.378(3)
C11 C12 1.378(3)
C12 C13 1.380(3)
C12 H12 0.9300
C13 C14 1.366(4)
C13 H13 0.9300
C14 C15 1.361(4)
C14 H14 0.9300
C15 C16 1.395(4)
C15 H15 0.9300
C16 H16 0.9300
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
N H O2 8_665 0.80(2) 2.09(3) 2.885(2) 169(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 C1 C2 C3 -0.3(3)
Cl1 C1 C2 C3 178.82(16)
C1 C2 C3 C5 -0.3(3)
C1 C2 C3 C4 -179.0(2)
C2 C3 C5 C6 0.3(3)
C4 C3 C5 C6 179.0(2)
C3 C5 C6 C7 0.3(3)
C8 O1 C7 C6 9.4(3)
C8 O1 C7 C1 -171.68(17)
C5 C6 C7 O1 178.02(19)
C5 C6 C7 C1 -0.9(3)
C2 C1 C7 O1 -178.11(18)
Cl1 C1 C7 O1 2.7(2)
C2 C1 C7 C6 0.9(3)
Cl1 C1 C7 C6 -178.22(16)
C7 O1 C8 C9 71.4(2)
C10 N C9 O2 2.8(3)
C10 N C9 C8 -174.4(2)
O1 C8 C9 O2 10.6(3)
O1 C8 C9 N -172.11(19)
C9 N C10 C11 168.6(2)
N C10 C11 C16 83.7(3)
N C10 C11 C12 -96.4(2)
C16 C11 C12 C13 0.8(3)
C10 C11 C12 C13 -179.1(2)
C11 C12 C13 C14 -0.1(4)
C12 C13 C14 C15 -0.8(4)
C13 C14 C15 C16 1.0(4)
C12 C11 C16 C15 -0.5(3)
C10 C11 C16 C15 179.4(2)
C14 C15 C16 C11 -0.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740451
