#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/77/2217787.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_2217787
loop_
_publ_author_name
'Luo, Wei'
'Liu, Rui'
'Li, Yu-Hao'
'Chen, Wei'
'Zhu, Hong-Jun'
_publ_section_title
;
 4-Iodo-2-methylaniline
;
_journal_coeditor_code           HK2418
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o591
_journal_paper_doi               10.1107/S1600536808004145
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H8 I N'
_chemical_formula_moiety         'C7 H8 I N'
_chemical_formula_sum            'C7 H8 I N'
_chemical_formula_weight         233.04
_chemical_melting_point          360
_chemical_name_common            4-iodo-2-methylbenzenamine
_chemical_name_systematic
;
4-Iodo-2-methylaniline
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5910(11)
_cell_length_b                   8.9410(18)
_cell_length_c                   15.674(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     783.5(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON-10M (Spek, 2003)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            917
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.000
_exptl_absorpt_correction_T_max  0.6698
_exptl_absorpt_correction_T_min  0.4867
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.961
_refine_ls_abs_structure_details 'Flack (1983), with no Friedel pairs'
_refine_ls_abs_structure_Flack   -0.29(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0445
_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)+(0.1P)²+1.0P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                737
_reflns_number_total             917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2418.cif
_cod_data_source_block           I
_cod_database_code               2217787
_cod_database_fobs_code          2217787
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_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
I I 0.01067(18) 0.20097(9) 0.23728(5) 0.0696(4) Uani d . 1
N N 0.407(2) 0.6567(10) -0.0309(8) 0.063(3) Uani d . 1
H H0A 0.3335 0.6711 -0.0784 0.076 Uiso calc R 1
H H0B 0.5326 0.7081 -0.0188 0.076 Uiso calc R 1
C C1 0.1534(18) 0.3484(11) 0.1464(7) 0.044(2) Uani d . 1
C C2 0.360(2) 0.4273(12) 0.1643(8) 0.053(3) Uani d . 1
H H2A 0.4425 0.4137 0.2152 0.063 Uiso calc R 1
C C3 0.439(2) 0.5276(13) 0.1030(7) 0.054(3) Uani d . 1
H H3A 0.5772 0.5825 0.1139 0.064 Uiso calc R 1
C C4 0.322(2) 0.5491(11) 0.0269(7) 0.042(2) Uani d . 1
C C5 0.122(2) 0.4658(11) 0.0088(7) 0.045(2) Uani d . 1
C C6 0.028(2) 0.3671(11) 0.0701(7) 0.051(3) Uani d . 1
H H6A -0.1143 0.3158 0.0601 0.062 Uiso calc R 1
C C7 -0.011(2) 0.4852(13) -0.0736(7) 0.059(3) Uani d . 1
H H7A -0.1480 0.4207 -0.0741 0.089 Uiso calc R 1
H H7B 0.0924 0.4599 -0.1204 0.089 Uiso calc R 1
H H7C -0.0615 0.5873 -0.0791 0.089 Uiso calc R 1
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
I 0.0908(7) 0.0662(5) 0.0517(5) -0.0067(5) 0.0050(5) 0.0104(3)
N 0.061(6) 0.051(5) 0.078(7) -0.004(5) 0.007(6) 0.012(5)
C1 0.048(6) 0.044(5) 0.038(5) 0.002(5) 0.011(5) -0.001(4)
C2 0.056(7) 0.052(6) 0.050(6) -0.005(5) -0.005(6) -0.005(5)
C3 0.041(6) 0.055(7) 0.064(7) -0.001(5) 0.001(5) -0.010(6)
C4 0.040(6) 0.043(6) 0.043(5) 0.006(4) 0.009(5) -0.002(4)
C5 0.058(7) 0.036(5) 0.040(5) 0.005(5) 0.002(5) 0.001(4)
C6 0.056(7) 0.044(5) 0.054(6) -0.005(6) -0.001(6) -0.006(4)
C7 0.063(7) 0.065(6) 0.050(5) 0.013(9) -0.009(8) -0.006(5)
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'
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
C4 N H0A 120.0
C4 N H0B 120.0
H0A N H0B 120.0
C2 C1 C6 122.2(10)
C2 C1 I 120.0(8)
C6 C1 I 117.7(8)
C1 C2 C3 117.2(10)
C1 C2 H2A 121.4
C3 C2 H2A 121.4
C4 C3 C2 122.7(10)
C4 C3 H3A 118.6
C2 C3 H3A 118.6
C5 C4 C3 119.4(10)
C5 C4 N 120.9(11)
C3 C4 N 119.7(11)
C4 C5 C6 120.3(10)
C4 C5 C7 121.2(10)
C6 C5 C7 118.3(11)
C1 C6 C5 118.1(10)
C1 C6 H6A 121.0
C5 C6 H6A 121.0
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I C1 2.099(10)
N H0A 0.8600
N H0B 0.8600
C1 C2 1.383(15)
C1 C6 1.397(15)
C2 C3 1.386(16)
C2 H2A 0.9300
C3 C4 1.375(16)
C3 H3A 0.9300
C4 C5 1.374(16)
C4 N 1.403(13)
C5 C6 1.408(15)
C6 H6A 0.9300
C7 C5 1.500(15)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 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
_geom_hbond_publ_flag
N H0B N 4_565 0.86 2.54 3.397(15) 174.00 yes
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
C6 C1 C2 C3 0.2(16)
I C1 C2 C3 -177.3(8)
C2 C1 C6 C5 2.5(16)
I C1 C6 C5 180.0(7)
C1 C2 C3 C4 -0.5(17)
C2 C3 C4 C5 -1.8(17)
C2 C3 C4 N 177.5(10)
C3 C4 C5 C6 4.6(16)
N C4 C5 C6 -174.8(9)
C3 C4 C5 C7 -179.8(10)
N C4 C5 C7 0.8(15)
C4 C5 C6 C1 -4.9(16)
C7 C5 C6 C1 179.4(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 75086
