#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221528.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_2221528
loop_
_publ_author_name
'Luger, Peter'
'Weber, Manuela'
'Thang, Tran Dinh'
'Van Luu, Hoang'
'Dung, Nguyen Xuan'
_publ_section_title
;
 N-Methyl-N-styrylcinnamamide (lansamide) from
 Clausena lansium in Vietnam
;
_journal_coeditor_code           TK2394
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o809
_journal_paper_doi               10.1107/S1600536809009611
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H17 N O'
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33
_chemical_name_systematic
;
N-Methyl-N-styrylcinnamamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.45(3)
_cell_angle_beta                 77.22(3)
_cell_angle_gamma                78.13(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3560(10)
_cell_length_b                   9.265(2)
_cell_length_c                   13.073(3)
_cell_measurement_reflns_used    5327
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      33.3
_cell_measurement_theta_min      2.3
_cell_volume                     728.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and SCHAKAL99 (Keller & Pierrard,
1999)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.023
_diffrn_reflns_av_sigmaI/netI    0.012
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            25654
_diffrn_reflns_theta_full        33.3
_diffrn_reflns_theta_max         33.3
_diffrn_reflns_theta_min         2.3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.55
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.079
_refine_ls_R_factor_gt           0.060
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0892P)²+0.1313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.162
_refine_ls_wR_factor_ref         0.190
_reflns_number_gt                3962
_reflns_number_total             5327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2394.cif
_cod_data_source_block           I
_cod_database_code               2221528
_cod_database_fobs_code          2221528
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6509(2) 0.21826(15) 0.99509(11) 0.0553(3) Uani d . 1 . .
H H1 0.5292 0.2328 0.9636 0.066 Uiso calc R 1 . .
C C2 0.6807(3) 0.10113(17) 1.07380(11) 0.0650(4) Uani d . 1 . .
H H2 0.5794 0.0373 1.0949 0.078 Uiso calc R 1 . .
C C3 0.8605(3) 0.07815(17) 1.12150(11) 0.0653(4) Uani d . 1 . .
H H3 0.8807 -0.0014 1.1742 0.078 Uiso calc R 1 . .
C C4 1.0085(3) 0.17266(18) 1.09103(12) 0.0671(4) Uani d . 1 . .
H H4 1.1283 0.1585 1.1238 0.080 Uiso calc R 1 . .
C C5 0.9801(2) 0.28959(16) 1.01128(11) 0.0581(3) Uani d . 1 . .
H H5 1.0830 0.3523 0.9902 0.070 Uiso calc R 1 . .
C C6 0.80051(19) 0.31483(12) 0.96224(9) 0.0447(2) Uani d . 1 . .
C C7 0.77651(19) 0.44124(13) 0.87988(9) 0.0469(2) Uani d . 1 . .
H H7 0.8947 0.4911 0.8572 0.056 Uiso calc R 1 . .
C C8 0.60545(19) 0.49270(12) 0.83399(9) 0.0447(2) Uani d . 1 . .
H H8 0.4831 0.4467 0.8541 0.054 Uiso calc R 1 . .
C C9 0.60632(18) 0.62255(12) 0.75108(9) 0.0439(2) Uani d . 1 . .
O O1 0.74616(16) 0.70168(10) 0.73318(8) 0.0600(2) Uani d . 1 . .
N N1 0.44089(16) 0.65399(10) 0.69570(8) 0.0474(2) Uani d . 1 . .
C C10 0.2872(2) 0.56144(15) 0.69998(10) 0.0537(3) Uani d . 1 . .
H H10 0.1398 0.6040 0.7155 0.064 Uiso calc R 1 . .
C C11 0.3327(2) 0.41992(15) 0.68402(10) 0.0545(3) Uani d . 1 . .
H H11 0.2124 0.3729 0.6941 0.065 Uiso calc R 1 . .
C C12 0.5480(2) 0.32715(12) 0.65251(9) 0.0472(3) Uani d . 1 . .
C C13 0.5818(3) 0.17475(15) 0.68682(12) 0.0663(4) Uani d . 1 . .
H H13 0.4678 0.1327 0.7309 0.080 Uiso calc R 1 . .
C C14 0.7817(4) 0.08498(16) 0.65648(15) 0.0781(5) Uani d . 1 . .
H H14 0.8016 -0.0160 0.6811 0.094 Uiso calc R 1 . .
C C15 0.9499(3) 0.14446(17) 0.59047(15) 0.0727(4) Uani d . 1 . .
H H15 1.0847 0.0843 0.5707 0.087 Uiso calc R 1 . .
C C16 0.9191(3) 0.29425(15) 0.55317(12) 0.0622(3) Uani d . 1 . .
H H16 1.0325 0.3345 0.5071 0.075 Uiso calc R 1 . .
C C17 0.7205(2) 0.38448(12) 0.58411(10) 0.0512(3) Uani d . 1 . .
H H17 0.7019 0.4853 0.5588 0.061 Uiso calc R 1 . .
C C18 0.4179(3) 0.79342(14) 0.62545(12) 0.0628(4) Uani d . 1 . .
H H181 0.4671 0.8674 0.6533 0.094 Uiso calc R 1 . .
H H182 0.2669 0.8259 0.6201 0.094 Uiso calc R 1 . .
H H183 0.5048 0.7788 0.5567 0.094 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
C2 C1 C6 . . 120.79(13) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 120.35(14) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.77(13) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.01(13) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.19(14) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C1 C6 C5 . . 117.88(11) ?
C1 C6 C7 . . 123.17(11) ?
C5 C6 C7 . . 118.95(11) ?
C8 C7 C6 . . 127.28(11) ?
C8 C7 H7 . . 116.4 ?
C6 C7 H7 . . 116.4 ?
C7 C8 C9 . . 120.86(11) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
O1 C9 N1 . . 120.39(11) ?
O1 C9 C8 . . 122.32(10) ?
N1 C9 C8 . . 117.28(10) ?
C9 N1 C10 . . 125.32(10) ?
C9 N1 C18 . . 118.41(11) ?
C10 N1 C18 . . 116.27(10) ?
C11 C10 N1 . . 126.33(11) ?
C11 C10 H10 . . 116.8 ?
N1 C10 H10 . . 116.8 ?
C10 C11 C12 . . 128.68(11) ?
C10 C11 H11 . . 115.7 ?
C12 C11 H11 . . 115.7 ?
C17 C12 C13 . . 117.46(13) ?
C17 C12 C11 . . 122.16(11) ?
C13 C12 C11 . . 120.30(12) ?
C14 C13 C12 . . 121.25(14) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C15 C14 C13 . . 120.15(13) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 119.79(16) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.21(15) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C12 . . 121.10(12) ?
C16 C17 H17 . . 119.5 ?
C12 C17 H17 . . 119.5 ?
N1 C18 H181 . . 109.5 ?
N1 C18 H182 . . 109.5 ?
H181 C18 H182 . . 109.5 ?
N1 C18 H183 . . 109.5 ?
H181 C18 H183 . . 109.5 ?
H182 C18 H183 . . 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
C1 C2 . 1.3798(19) ?
C1 C6 . 1.3896(18) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.383(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.366(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3902(17) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.4611(16) ?
C7 C8 . 1.3228(16) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4797(16) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.2254(15) ?
C9 N1 . 1.3621(15) ?
N1 C10 . 1.4133(17) ?
N1 C18 . 1.4566(16) ?
C10 C11 . 1.3245(19) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.471(2) ?
C11 H11 . 0.9300 ?
C12 C17 . 1.3902(18) ?
C12 C13 . 1.3960(17) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.367(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.381(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.381(2) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H181 . 0.9600 ?
C18 H182 . 0.9600 ?
C18 H183 . 0.9600 ?
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
C6 C1 C2 C3 . . . . 0.1(2) ?
C1 C2 C3 C4 . . . . 0.5(2) ?
C2 C3 C4 C5 . . . . -1.1(2) ?
C3 C4 C5 C6 . . . . 1.1(2) ?
C2 C1 C6 C5 . . . . -0.1(2) ?
C2 C1 C6 C7 . . . . -179.54(12) ?
C4 C5 C6 C1 . . . . -0.5(2) ?
C4 C5 C6 C7 . . . . 178.95(12) ?
C1 C6 C7 C8 . . . . 8.2(2) ?
C5 C6 C7 C8 . . . . -171.22(12) ?
C6 C7 C8 C9 . . . . -179.88(10) ?
C7 C8 C9 O1 . . . . -11.86(18) ?
C7 C8 C9 N1 . . . . 169.57(11) ?
O1 C9 N1 C10 . . . . 171.70(11) ?
C8 C9 N1 C10 . . . . -9.70(17) ?
O1 C9 N1 C18 . . . . -7.99(17) ?
C8 C9 N1 C18 . . . . 170.62(10) ?
C9 N1 C10 C11 . . . . -53.69(19) ?
C18 N1 C10 C11 . . . . 126.00(14) ?
N1 C10 C11 C12 . . . . -3.9(2) ?
C10 C11 C12 C17 . . . . -34.6(2) ?
C10 C11 C12 C13 . . . . 148.71(14) ?
C17 C12 C13 C14 . . . . 1.9(2) ?
C11 C12 C13 C14 . . . . 178.75(13) ?
C12 C13 C14 C15 . . . . -1.0(2) ?
C13 C14 C15 C16 . . . . -0.7(3) ?
C14 C15 C16 C17 . . . . 1.3(2) ?
C15 C16 C17 C12 . . . . -0.3(2) ?
C13 C12 C17 C16 . . . . -1.29(19) ?
C11 C12 C17 C16 . . . . -178.04(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9532444
