#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/92/2009259.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_2009259
loop_
_publ_author_name
'Shanmuga Sundara Raj, S.'
'Renganayaki, S.'
'Subramanian, E.'
'Fun, Hoong-Kun'
_publ_section_title
;
 N-Benzyl-N-(2-iodo-4-methylphenyl)cinnamamide and
 N-benzyl-N-(p-tolyl)cinnamamide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2182
_journal_page_last               2184
_journal_paper_doi               10.1107/S0108270199011749
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C23 H20 I N O'
_chemical_formula_weight         453.30
_chemical_name_systematic
;
N-benzyl-N-(2-iodo-4-methylphenyl)cinnamamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.4980(10)
_cell_angle_beta                 103.2620(10)
_cell_angle_gamma                90.2840(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3376(4)
_cell_length_b                   10.1794(4)
_cell_length_c                   10.9289(5)
_cell_measurement_reflns_used    4581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.92
_cell_volume                     1006.06(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'ω scan'
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.038
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7002
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    1.602
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.99
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.043
_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)+(0.0501P)²+0.7590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.119
_reflns_number_gt                3598
_reflns_number_total             4807
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1216.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2009259
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
I1 0.03476(3) 0.73959(3) 0.90792(3) 0.07664(14) Uani d . 1 . . I
C1 -0.1168(3) 0.6766(3) 1.4136(3) 0.0440(7) Uani d . 1 . . C
C2 -0.1229(4) 0.5449(3) 1.3634(3) 0.0485(7) Uani d . 1 . . C
H2A -0.0725 0.5199 1.3011 0.058 Uiso calc R 1 . . H
C3 -0.2029(4) 0.4516(4) 1.4050(4) 0.0609(9) Uani d . 1 . . C
H3A -0.2063 0.3642 1.3705 0.073 Uiso calc R 1 . . H
C4 -0.2778(5) 0.4870(5) 1.4974(4) 0.0714(11) Uani d . 1 . . C
H4A -0.3328 0.4239 1.5243 0.086 Uiso calc R 1 . . H
C5 -0.2712(6) 0.6157(5) 1.5496(5) 0.0791(13) Uani d . 1 . . C
H5A -0.3198 0.6394 1.6135 0.095 Uiso calc R 1 . . H
C6 -0.1923(5) 0.7101(4) 1.5074(4) 0.0655(10) Uani d . 1 . . C
H6A -0.1898 0.7973 1.5423 0.079 Uiso calc R 1 . . H
C7 -0.0341(4) 0.7797(3) 1.3724(3) 0.0464(7) Uani d . 1 . . C
H7A -0.0451 0.8656 1.4056 0.056 Uiso calc R 1 . . H
C8 0.0541(4) 0.7653(3) 1.2938(3) 0.0471(7) Uani d . 1 . . C
H8A 0.0707 0.6811 1.2595 0.057 Uiso calc R 1 . . H
C9 0.1273(3) 0.8816(3) 1.2594(3) 0.0472(7) Uani d . 1 . . C
O10 0.0990(3) 0.9951(2) 1.2931(3) 0.0642(7) Uani d . 1 . . O
N11 0.2249(3) 0.8573(3) 1.1848(3) 0.0479(6) Uani d . 1 . . N
C12 0.2940(4) 0.9677(3) 1.1392(4) 0.0544(8) Uani d . 1 . . C
H12A 0.2332 1.0444 1.1417 0.065 Uiso calc R 1 . . H
H12B 0.2975 0.9440 1.0518 0.065 Uiso calc R 1 . . H
C13 0.4475(4) 1.0038(3) 1.2152(3) 0.0466(7) Uani d . 1 . . C
C14 0.4731(5) 1.0706(4) 1.3352(4) 0.0695(11) Uani d . 1 . . C
H14A 0.3943 1.0933 1.3710 0.083 Uiso calc R 1 . . H
C15 0.6157(6) 1.1039(5) 1.4020(5) 0.0849(14) Uani d . 1 . . C
H15A 0.6317 1.1484 1.4825 0.102 Uiso calc R 1 . . H
C16 0.7327(5) 1.0721(4) 1.3508(5) 0.0773(12) Uani d . 1 . . C
H16A 0.8280 1.0952 1.3960 0.093 Uiso calc R 1 . . H
C17 0.7095(5) 1.0066(4) 1.2339(5) 0.0690(11) Uani d . 1 . . C
H17A 0.7891 0.9853 1.1987 0.083 Uiso calc R 1 . . H
C18 0.5680(4) 0.9713(4) 1.1663(4) 0.0551(8) Uani d . 1 . . C
H18A 0.5538 0.9250 1.0867 0.066 Uiso calc R 1 . . H
C19 0.2699(3) 0.7269(3) 1.1503(3) 0.0435(6) Uani d . 1 . . C
C20 0.3862(4) 0.6716(4) 1.2303(4) 0.0559(8) Uani d . 1 . . C
H20A 0.4358 0.7198 1.3047 0.067 Uiso calc R 1 . . H
C21 0.4285(5) 0.5452(4) 1.1997(4) 0.0657(10) Uani d . 1 . . C
H21A 0.5062 0.5091 1.2544 0.079 Uiso calc R 1 . . H
C22 0.3580(5) 0.4713(4) 1.0900(4) 0.0633(10) Uani d . 1 . . C
C23 0.2447(5) 0.5271(4) 1.0083(4) 0.0604(9) Uani d . 1 . . C
H23A 0.1966 0.4790 0.9334 0.072 Uiso calc R 1 . . H
C24 0.2017(4) 0.6551(3) 1.0375(3) 0.0501(7) Uani d . 1 . . C
C25 0.4018(7) 0.3313(4) 1.0564(6) 0.0955(18) Uani d . 1 . . C
H25A 0.4815 0.3068 1.1220 0.143 Uiso calc R 1 . . H
H25B 0.4324 0.3267 0.9780 0.143 Uiso calc R 1 . . H
H25C 0.3192 0.2719 1.0479 0.143 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'
I I -0.4742 1.8119 '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_publ_flag
C6 C1 C2 118.0(3) ?
C6 C1 C7 119.1(3) ?
C2 C1 C7 122.9(3) ?
C3 C2 C1 120.7(3) ?
C4 C3 C2 120.4(4) ?
C5 C4 C3 119.9(4) ?
C4 C5 C6 120.1(4) ?
C5 C6 C1 121.0(4) ?
C8 C7 C1 127.8(3) y
C7 C8 C9 120.9(3) ?
O10 C9 N11 120.9(3) ?
O10 C9 C8 122.0(3) ?
N11 C9 C8 117.1(3) ?
C9 N11 C19 123.1(3) y
C9 N11 C12 120.3(3) y
C19 N11 C12 116.6(3) y
N11 C12 C13 113.4(3) ?
C18 C13 C14 117.8(4) ?
C18 C13 C12 120.5(3) ?
C14 C13 C12 121.8(3) ?
C15 C14 C13 120.3(4) ?
C16 C15 C14 120.7(4) ?
C17 C16 C15 119.7(4) ?
C16 C17 C18 120.4(4) ?
C13 C18 C17 121.1(4) ?
C24 C19 C20 118.7(3) ?
C24 C19 N11 121.7(3) ?
C20 C19 N11 119.6(3) ?
C21 C20 C19 120.2(4) ?
C22 C21 C20 121.5(4) ?
C21 C22 C23 118.6(3) ?
C21 C22 C25 122.0(4) ?
C23 C22 C25 119.4(5) ?
C22 C23 C24 120.5(4) ?
C19 C24 C23 120.4(3) ?
C19 C24 I1 120.1(2) ?
C23 C24 I1 119.5(3) ?
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
I1 C24 . 2.100(3) y
C1 C6 . 1.390(5) ?
C1 C2 . 1.395(5) ?
C1 C7 . 1.463(5) y
C2 C3 . 1.378(5) ?
C3 C4 . 1.377(6) ?
C4 C5 . 1.373(7) ?
C5 C6 . 1.383(6) ?
C7 C8 . 1.319(5) y
C8 C9 . 1.486(4) y
C9 O10 . 1.228(4) y
C9 N11 . 1.363(4) y
N11 C19 . 1.436(4) y
N11 C12 . 1.475(4) y
C12 C13 . 1.506(5) ?
C13 C18 . 1.380(5) ?
C13 C14 . 1.387(5) ?
C14 C15 . 1.386(7) ?
C15 C16 . 1.365(7) ?
C16 C17 . 1.353(7) ?
C17 C18 . 1.385(6) ?
C19 C24 . 1.387(5) ?
C19 C20 . 1.388(5) ?
C20 C21 . 1.381(6) ?
C21 C22 . 1.377(6) ?
C22 C23 . 1.382(6) ?
C22 C25 . 1.519(6) y
C23 C24 . 1.394(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652260
