#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/11/2201184.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_2201184
loop_
_publ_author_name
'Chen, Xuanhua'
'Guo, Rongwei'
'Zhou, Zhongyuan'
_publ_section_title
;
 N-[2-Methyl-1-(2-naphthyl)propenyl]acetamide
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o568
_journal_page_last               o569
_journal_paper_doi               10.1107/S1600536802007079
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C16 H17 N O'
_chemical_formula_moiety         'C16 H17 N O'
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.31
_chemical_name_systematic
;
N-[2-methyl-1-(2-naphthyl)propenyl]acetamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9766(14)
_cell_length_b                   12.3744(19)
_cell_length_c                   12.4145(18)
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1379.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SHELXTL-NT (Siemens, 1995)'
_computing_molecular_graphics    SHELXTL-NT
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker 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  0.072
_diffrn_reflns_av_sigmaI/netI    0.064
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9481
_diffrn_reflns_theta_full        27.6
_diffrn_reflns_theta_max         27.6
_diffrn_reflns_theta_min         3.3
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.10
_refine_diff_density_min         -0.10
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.94
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.94
_refine_ls_R_factor_all          0.107
_refine_ls_R_factor_gt           0.035
_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)+(0.015P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.056
_refine_ls_wR_factor_ref         0.065
_reflns_number_gt                828
_reflns_number_total             1823
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6051.cif
_cod_data_source_block           I
_cod_database_code               2201184
_cod_database_fobs_code          2201184
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'
loop_
_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
_atom_site_type_symbol
O1 0.4357(2) 0.67851(15) 0.49420(15) 0.0796(6) Uani d . 1 . . O
N1 0.2095(2) 0.72939(16) 0.43428(15) 0.0601(6) Uani d . 1 . . N
H1A 0.1294 0.7645 0.4492 0.072 Uiso calc R 1 . . H
C1 0.2496(3) 0.7499(2) 0.24112(18) 0.0536(6) Uani d . 1 . . C
C2 0.1689(3) 0.7496(2) 0.14753(19) 0.0605(7) Uani d . 1 . . C
H2A 0.0888 0.7024 0.1416 0.073 Uiso calc R 1 . . H
C3 0.2021(3) 0.8177(2) 0.0599(2) 0.0565(7) Uani d . 1 . . C
C4 0.1207(3) 0.8155(2) -0.0374(2) 0.0704(8) Uani d . 1 . . C
H4A 0.0397 0.7690 -0.0440 0.084 Uiso calc R 1 . . H
C5 0.1584(4) 0.8793(3) -0.1208(2) 0.0831(9) Uani d . 1 . . C
H5A 0.1034 0.8766 -0.1842 0.100 Uiso calc R 1 . . H
C6 0.2783(4) 0.9491(3) -0.1129(2) 0.0858(9) Uani d . 1 . . C
H6A 0.3047 0.9914 -0.1718 0.103 Uiso calc R 1 . . H
C7 0.3581(3) 0.9565(2) -0.0200(2) 0.0724(8) Uani d . 1 . . C
H7A 0.4363 1.0056 -0.0149 0.087 Uiso calc R 1 . . H
C8 0.3225(3) 0.8899(2) 0.0688(2) 0.0589(7) Uani d . 1 . . C
C9 0.4010(3) 0.8934(2) 0.1664(2) 0.0667(8) Uani d . 1 . . C
H9A 0.4770 0.9438 0.1750 0.080 Uiso calc R 1 . . H
C10 0.3684(3) 0.8249(2) 0.2489(2) 0.0656(8) Uani d . 1 . . C
H10A 0.4252 0.8273 0.3115 0.079 Uiso calc R 1 . . H
C11 0.2185(3) 0.6760(2) 0.33180(19) 0.0546(7) Uani d . 1 . . C
C12 0.1977(3) 0.5698(2) 0.3247(2) 0.0662(7) Uani d . 1 . . C
C13 0.2180(4) 0.5066(2) 0.22083(18) 0.0902(10) Uani d . 1 . . C
H13A 0.2714 0.5500 0.1697 0.135 Uiso calc R 1 . . H
H13B 0.1222 0.4881 0.1919 0.135 Uiso calc R 1 . . H
H13C 0.2733 0.4418 0.2353 0.135 Uiso calc R 1 . . H
C14 0.1606(3) 0.5007(2) 0.4207(2) 0.0966(10) Uani d . 1 . . C
H14A 0.1307 0.5461 0.4796 0.145 Uiso calc R 1 . . H
H14B 0.2466 0.4595 0.4413 0.145 Uiso calc R 1 . . H
H14C 0.0807 0.4525 0.4026 0.145 Uiso calc R 1 . . H
C15 0.3184(3) 0.7280(2) 0.5082(2) 0.0613(7) Uani d . 1 . . C
C16 0.2898(3) 0.7921(2) 0.60835(17) 0.0756(8) Uani d . 1 . . C
H16A 0.3324 0.7554 0.6691 0.113 Uiso calc R 1 . . H
H16D 0.1844 0.7998 0.6188 0.113 Uiso calc R 1 . . H
H16C 0.3344 0.8623 0.6014 0.113 Uiso calc R 1 . . H
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
C15 N1 C11 124.0(2)
C15 N1 H1A 118.0
C11 N1 H1A 118.0
C2 C1 C10 117.2(2)
C2 C1 C11 123.0(2)
C10 C1 C11 119.7(2)
C1 C2 C3 122.8(2)
C1 C2 H2A 118.6
C3 C2 H2A 118.6
C8 C3 C2 118.8(2)
C8 C3 C4 118.5(3)
C2 C3 C4 122.6(3)
C5 C4 C3 121.1(3)
C5 C4 H4A 119.5
C3 C4 H4A 119.5
C4 C5 C6 120.5(3)
C4 C5 H5A 119.7
C6 C5 H5A 119.7
C7 C6 C5 120.8(3)
C7 C6 H6A 119.6
C5 C6 H6A 119.6
C6 C7 C8 120.1(3)
C6 C7 H7A 119.9
C8 C7 H7A 119.9
C9 C8 C3 118.3(2)
C9 C8 C7 122.8(3)
C3 C8 C7 118.9(3)
C10 C9 C8 121.5(3)
C10 C9 H9A 119.3
C8 C9 H9A 119.3
C9 C10 C1 121.2(2)
C9 C10 H10A 119.4
C1 C10 H10A 119.4
C12 C11 N1 120.3(2)
C12 C11 C1 126.0(2)
N1 C11 C1 113.6(2)
C11 C12 C14 122.7(2)
C11 C12 C13 123.2(2)
C14 C12 C13 114.0(2)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O1 C15 N1 122.3(2)
O1 C15 C16 121.9(2)
N1 C15 C16 115.9(2)
C15 C16 H16A 109.5
C15 C16 H16D 109.5
H16A C16 H16D 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16D C16 H16C 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
O1 C15 . 1.230(3) ?
N1 C15 . 1.341(3) ?
N1 C11 . 1.436(3) ?
N1 H1A . 0.8600 ?
C1 C2 . 1.369(3) ?
C1 C10 . 1.417(3) ?
C1 C11 . 1.477(3) ?
C2 C3 . 1.408(3) ?
C2 H2A . 0.9300 ?
C3 C8 . 1.406(3) ?
C3 C4 . 1.413(3) ?
C4 C5 . 1.346(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.383(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.361(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.414(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.402(3) ?
C9 C10 . 1.362(3) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.331(3) ?
C12 C14 . 1.504(3) ?
C12 C13 . 1.519(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.497(3) ?
C16 H16A . 0.9600 ?
C16 H16D . 0.9600 ?
C16 H16C . 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
N1 H1A O1 4_466 0.86 2.00 2.852(3) 168.1
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
C10 C1 C2 C3 1.7(4)
C11 C1 C2 C3 -177.8(2)
C1 C2 C3 C8 -0.5(4)
C1 C2 C3 C4 178.5(2)
C8 C3 C4 C5 1.1(4)
C2 C3 C4 C5 -177.9(3)
C3 C4 C5 C6 0.0(5)
C4 C5 C6 C7 -1.7(5)
C5 C6 C7 C8 2.3(4)
C2 C3 C8 C9 -2.3(3)
C4 C3 C8 C9 178.7(2)
C2 C3 C8 C7 178.6(2)
C4 C3 C8 C7 -0.5(4)
C6 C7 C8 C9 179.7(3)
C6 C7 C8 C3 -1.2(4)
C3 C8 C9 C10 3.9(4)
C7 C8 C9 C10 -177.0(2)
C8 C9 C10 C1 -2.7(4)
C2 C1 C10 C9 -0.1(4)
C11 C1 C10 C9 179.4(2)
C15 N1 C11 C12 78.0(3)
C15 N1 C11 C1 -102.8(3)
C2 C1 C11 C12 48.1(4)
C10 C1 C11 C12 -131.4(3)
C2 C1 C11 N1 -131.2(2)
C10 C1 C11 N1 49.4(3)
N1 C11 C12 C14 1.6(4)
C1 C11 C12 C14 -177.5(3)
N1 C11 C12 C13 -174.8(2)
C1 C11 C12 C13 6.0(5)
C11 N1 C15 O1 -1.1(4)
C11 N1 C15 C16 177.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132359
