#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:17:34 +0100 (jue 24 de mar de 2016) $
#$Revision: 179622 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/86/4508672.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508672
loop_
_publ_author_name
'Merz, Klaus'
_publ_section_title
;
 Substitution Effect on Crystal Packings of Iodobenzonitriles and
 Iodophenols
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1615
_journal_paper_doi               10.1021/cg060067j
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C6 H5 I O'
_chemical_formula_weight         220.00
_chemical_name_systematic
; 
 ? 
;
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.629(2)
_cell_length_b                   9.534(4)
_cell_length_c                   14.913(7)
_cell_measurement_reflns_used    694
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      4.61
_cell_volume                     658.2(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Siemens, 1996)'
_computing_structure_refinement  'SHELXTL (Siemens, 1996)'
_computing_structure_solution    'SHELXTL (Siemens, 1996)'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker axs CCD 1000'
_diffrn_measurement_method       omega-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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1671
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        -
_diffrn_standards_interval_count -
_diffrn_standards_interval_time  -
_diffrn_standards_number         -
_exptl_absorpt_coefficient_mu    4.761
_exptl_absorpt_correction_T_max  0.6474
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   'empirical Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.220
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0231
_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)+(0.0309P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0596
_reflns_number_gt                949
_reflns_number_total             999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060067jsup1.cif
_cod_data_source_block           051109t
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4508672
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.13407(8) 0.56169(4) 0.69827(2) 0.04000(15) Uani 1 1 d .
C1 C 0.3709(10) 0.5605(6) 0.8191(3) 0.0301(10) Uani 1 1 d .
C2 C 0.3904(11) 0.4394(6) 0.8693(3) 0.0262(10) Uani 1 1 d .
H2A H 0.2903 0.3578 0.8523 0.031 Uiso 1 1 calc R
C4 C 0.7132(10) 0.5604(6) 0.9699(3) 0.0312(12) Uani 1 1 d .
H4A H 0.8328 0.5598 1.0208 0.037 Uiso 1 1 calc R
C3 C 0.5619(9) 0.4415(6) 0.9454(3) 0.0254(10) Uani 1 1 d .
C6 C 0.5135(12) 0.6806(7) 0.8435(4) 0.0330(12) Uani 1 1 d .
H6A H 0.4938 0.7628 0.8093 0.040 Uiso 1 1 calc R
C5 C 0.6862(12) 0.6793(7) 0.9189(3) 0.0366(13) Uani 1 1 d .
H5A H 0.7867 0.7609 0.9355 0.044 Uiso 1 1 calc R
O1 O 0.5917(9) 0.3244(4) 0.9990(2) 0.0330(8) Uani 1 1 d .
H1 H 0.449(14) 0.277(7) 1.002(5) 0.04(2) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0464(2) 0.0452(3) 0.02838(18) 0.00094(16) -0.00539(16) 0.0111(2)
C1 0.032(2) 0.031(3) 0.027(2) 0.002(2) 0.002(2) 0.010(3)
C2 0.026(2) 0.024(3) 0.029(2) -0.005(2) 0.0047(19) -0.002(3)
C4 0.029(3) 0.035(3) 0.029(2) -0.001(3) 0.0001(18) -0.003(3)
C3 0.025(2) 0.027(3) 0.024(2) 0.006(2) 0.0077(17) 0.008(2)
C6 0.041(3) 0.024(3) 0.035(3) 0.006(3) 0.008(2) 0.000(3)
C5 0.044(3) 0.031(3) 0.034(3) -0.005(3) 0.003(2) -0.006(3)
O1 0.031(2) 0.033(2) 0.0354(18) 0.0098(17) -0.0007(17) 0.000(2)
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'
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
C6 C1 C2 121.6(5)
C6 C1 I1 118.2(4)
C2 C1 I1 120.2(4)
C1 C2 C3 118.0(5)
C1 C2 H2A 121.0
C3 C2 H2A 121.0
C5 C4 C3 119.1(5)
C5 C4 H4A 120.5
C3 C4 H4A 120.5
O1 C3 C4 117.4(4)
O1 C3 C2 121.3(5)
C4 C3 C2 121.3(5)
C1 C6 C5 119.2(5)
C1 C6 H6A 120.4
C5 C6 H6A 120.4
C4 C5 C6 120.8(6)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C3 O1 H1 114(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.109(5)
C1 C6 1.371(8)
C1 C2 1.378(8)
C2 C3 1.386(7)
C2 H2A 0.9400
C4 C5 1.370(8)
C4 C3 1.381(8)
C4 H4A 0.9400
C3 O1 1.381(6)
C6 C5 1.380(8)
C6 H6A 0.9400
C5 H5A 0.9400
O1 H1 0.80(7)
