#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009034.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_2009034
loop_
_publ_author_name
'Renganayaki, S.'
'Subramanian, E.'
'Shanmuga Sundara Raj, S.'
'Fun, H.-K.'
_publ_section_title
;
N-(4-Chloro-2-iodophenyl)-N-methylcinnamamide
;
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 1672
_journal_page_last 1673
_journal_volume 55
_journal_year 1999
_chemical_formula_sum 'C16 H13 Cl I N O'
_chemical_formula_weight 397.62
_chemical_name_systematic
;
N-methyl-[o-iodo-p-chloro phenyl]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 79.1040(10)
_cell_angle_beta 64.8980(10)
_cell_angle_gamma 65.4560(10)
_cell_formula_units_Z 2
_cell_length_a 9.0587(2)
_cell_length_b 10.2616(2)
_cell_length_c 10.3295(2)
_cell_measurement_reflns_used 6563
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 28.37
_cell_measurement_theta_min 2.18
_cell_volume 790.85(3)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type 'Siemens SMART CCD area-detector'
_diffrn_measurement_method \w
_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 0.0362
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 5477
_diffrn_reflns_theta_full 28.28
_diffrn_reflns_theta_max 28.28
_diffrn_reflns_theta_min 2.18
_exptl_absorpt_coefficient_mu 2.188
_exptl_absorpt_correction_T_max 0.542
_exptl_absorpt_correction_T_min 0.393
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.670
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 388
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.28
_refine_diff_density_max 0.699
_refine_diff_density_min -0.705
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 181
_refine_ls_number_reflns 3771
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.042
_refine_ls_R_factor_all 0.048
_refine_ls_R_factor_gt 0.041
_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/[\s^2^(Fo^2^)+(0.0507P)^2^+0.5358P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_ref 0.114
_reflns_number_gt 3193
_reflns_number_total 3771
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file na1426.cif
_[local]_cod_data_source_block ccmm
_cod_database_code 2009034
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_type_symbol
I1 0.36433(4) 0.02306(3) 0.86830(3) 0.08116(14) Uani d . 1 I
Cl1 0.16166(15) 0.52496(14) 0.54081(14) 0.0886(3) Uani d . 1 Cl
C1 0.8049(4) 0.3011(4) 0.9076(3) 0.0523(6) Uani d . 1 C
C2 0.7279(6) 0.4353(4) 0.8562(4) 0.0691(9) Uani d . 1 C
H2A 0.6946 0.4432 0.7805 0.083 Uiso calc R 1 H
C3 0.6994(8) 0.5577(5) 0.9148(6) 0.0956(15) Uani d . 1 C
H3A 0.6465 0.6473 0.8793 0.115 Uiso calc R 1 H
C4 0.7500(8) 0.5468(7) 1.0268(6) 0.0987(16) Uani d . 1 C
H4A 0.7328 0.6293 1.0654 0.118 Uiso calc R 1 H
C5 0.8241(8) 0.4169(7) 1.0802(5) 0.0930(15) Uani d . 1 C
H5A 0.8554 0.4107 1.1568 0.112 Uiso calc R 1 H
C6 0.8543(5) 0.2918(5) 1.0214(4) 0.0693(9) Uani d . 1 C
H6A 0.9071 0.2026 1.0578 0.083 Uiso calc R 1 H
C7 0.8413(4) 0.1692(3) 0.8453(3) 0.0517(6) Uani d . 1 C
H7A 0.9243 0.0860 0.8649 0.062 Uiso calc R 1 H
C8 0.7684(4) 0.1556(3) 0.7637(3) 0.0514(6) Uani d . 1 C
H8A 0.6811 0.2350 0.7448 0.062 Uiso calc R 1 H
C9 0.8248(4) 0.0142(3) 0.7020(3) 0.0542(7) Uani d . 1 C
O10 0.9404(4) -0.0918(3) 0.7235(3) 0.0749(7) Uani d . 1 O
N11 0.7407(4) 0.0100(3) 0.6216(3) 0.0586(6) Uani d . 1 N
C12 0.7922(7) -0.1253(5) 0.5556(6) 0.0904(14) Uani d . 1 C
H12A 0.8876 -0.1979 0.5777 0.136 Uiso calc R 1 H
H12B 0.8290 -0.1119 0.4538 0.136 Uiso calc R 1 H
H12C 0.6937 -0.1544 0.5922 0.136 Uiso calc R 1 H
C13 0.6000(4) 0.1294(3) 0.5992(3) 0.0510(6) Uani d . 1 C
C14 0.6346(5) 0.2191(4) 0.4808(4) 0.0628(8) Uani d . 1 C
H14A 0.7495 0.1980 0.4142 0.075 Uiso calc R 1 H
C15 0.5005(5) 0.3397(5) 0.4604(4) 0.0662(8) Uani d . 1 C
H15A 0.5250 0.3995 0.3811 0.079 Uiso calc R 1 H
C16 0.3303(5) 0.3699(4) 0.5590(4) 0.0568(7) Uani d . 1 C
C17 0.2907(4) 0.2800(4) 0.6747(3) 0.0557(7) Uani d . 1 C
H17A 0.1749 0.3004 0.7392 0.067 Uiso calc R 1 H
C18 0.4252(4) 0.1592(3) 0.6937(3) 0.0511(6) Uani d . 1 C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0754(2) 0.0814(2) 0.07007(19) -0.03506(15) -0.01649(13) 0.01963(13)
Cl1 0.0721(6) 0.1041(8) 0.0940(7) -0.0320(6) -0.0490(6) 0.0272(6)
C1 0.0491(15) 0.0677(18) 0.0441(14) -0.0295(14) -0.0145(12) -0.0009(12)
C2 0.089(3) 0.065(2) 0.065(2) -0.0334(19) -0.0359(19) 0.0006(16)
C3 0.123(4) 0.070(3) 0.099(3) -0.041(3) -0.040(3) -0.008(2)
C4 0.118(4) 0.109(4) 0.089(3) -0.061(3) -0.029(3) -0.028(3)
C5 0.105(3) 0.136(5) 0.067(2) -0.067(3) -0.031(2) -0.020(3)
C6 0.069(2) 0.095(3) 0.0554(18) -0.039(2) -0.0277(16) 0.0030(18)
C7 0.0475(14) 0.0538(15) 0.0495(15) -0.0195(12) -0.0168(12) 0.0047(12)
C8 0.0487(15) 0.0465(14) 0.0558(16) -0.0138(12) -0.0199(13) -0.0046(12)
C9 0.0486(15) 0.0458(14) 0.0549(16) -0.0154(12) -0.0085(13) -0.0062(12)
O10 0.0645(15) 0.0512(13) 0.0886(18) -0.0044(11) -0.0259(14) -0.0072(12)
N11 0.0577(15) 0.0483(13) 0.0645(16) -0.0170(11) -0.0149(12) -0.0180(12)
C12 0.098(3) 0.064(2) 0.101(3) -0.025(2) -0.021(3) -0.037(2)
C13 0.0572(16) 0.0542(15) 0.0488(14) -0.0283(13) -0.0157(12) -0.0105(12)
C14 0.0598(18) 0.079(2) 0.0515(17) -0.0371(17) -0.0116(14) -0.0043(15)
C15 0.070(2) 0.084(2) 0.0544(18) -0.0435(19) -0.0243(16) 0.0115(16)
C16 0.0628(18) 0.0704(19) 0.0549(16) -0.0331(16) -0.0331(15) 0.0046(14)
C17 0.0536(16) 0.075(2) 0.0492(15) -0.0337(15) -0.0196(13) -0.0017(14)
C18 0.0569(16) 0.0606(16) 0.0431(13) -0.0320(14) -0.0155(12) -0.0031(12)
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'
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
C2 C1 C6 118.3(3) ?
C2 C1 C7 122.6(3) ?
C6 C1 C7 119.0(3) ?
C3 C2 C1 121.3(4) ?
C2 C3 C4 119.7(5) ?
C5 C4 C3 120.3(4) ?
C4 C5 C6 120.6(4) ?
C5 C6 C1 119.8(4) y
C8 C7 C1 126.8(3) y
C7 C8 C9 120.8(3) y
O10 C9 N11 122.1(3) y
O10 C9 C8 121.2(3) y
N11 C9 C8 116.7(3) y
C9 N11 C13 123.9(2) y
C9 N11 C12 119.4(3) y
C13 N11 C12 116.7(3) y
C14 C13 C18 118.4(3) ?
C14 C13 N11 120.1(3) ?
C18 C13 N11 121.5(3) ?
C15 C14 C13 121.0(3) ?
C16 C15 C14 119.2(3) ?
C15 C16 C17 121.2(3) ?
C15 C16 Cl1 120.1(3) ?
C17 C16 Cl1 118.7(3) ?
C16 C17 C18 119.2(3) ?
C17 C18 C13 120.8(3) ?
C17 C18 I1 119.1(2) ?
C13 C18 I1 120.1(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C18 2.086(3) y
Cl1 C16 1.736(4) y
C1 C2 1.380(5) ?
C1 C6 1.400(5) ?
C1 C7 1.461(5) y
C2 C3 1.377(6) ?
C3 C4 1.386(8) ?
C4 C5 1.351(8) ?
C5 C6 1.398(7) ?
C7 C8 1.326(4) y
C8 C9 1.493(4) y
C9 O10 1.220(4) y
C9 N11 1.360(5) ?
N11 C13 1.423(4) ?
N11 C12 1.470(4) ?
C13 C14 1.389(5) ?
C13 C18 1.398(4) ?
C14 C15 1.386(6) ?
C15 C16 1.379(5) ?
C16 C17 1.379(5) ?
C17 C18 1.384(5) ?
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
_geom_hbond_publ_flag
C14 H14A O10 2_756 0.93 2.40 3.309(6) 166 yes