#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/44/2004499.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_2004499
loop_
_publ_author_name
'Loll, P. J.'
'Garavito, R. M.'
'Carrell, C. J.'
'Carrell, H. L.'
_publ_section_title
;
 1-(4-Iodobenzoyl)-5-methoxy-2-methyl-3-indoleacetic Acid, an Iodinated
 Indomethacin Analog
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              455
_journal_page_last               457
_journal_paper_doi               10.1107/S0108270195010468
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C19 H16 I N O4'
_chemical_formula_weight         449.23
_chemical_melting_point          477.5
_chemical_name_common            iodoindomethacin
_chemical_name_systematic
;
1-(4-iodobenzoyl)-5-methoxy-2-methylindole-3-acetic acid
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5060(10)
_cell_length_b                   4.7250(10)
_cell_length_c                   19.166(8)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.8
_cell_measurement_theta_min      4.5
_cell_volume                     860.4(4)
_computing_cell_refinement       MADNES
_computing_data_collection       'MADNES (Messerschmidt & Pflugrath, 1987)'
_computing_data_reduction        MADNES
_computing_molecular_graphics
;
FRODO (Jones, 1982), ORTEPII (Johnson, 1976) and
PLUTO (Motherwell & Clegg, 1978)
;
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution
'CCP4 Suite (Collaborative Computational Project, Number 4, 1994)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Enraf-Nonius Fast area detector'
_diffrn_measurement_method       'rotation method, on-line box integration'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf-Nonius rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8940
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         No
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       blade
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.632
_refine_ls_abs_structure_details 'Flack (1983) parameter = 0.08(3)'
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.003
_refine_ls_goodness_of_fit_obs   1.110
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_restrained_S_obs      1.110
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_obs          0.0335
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0390P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0813
_refine_ls_wR_factor_obs         0.0786
_reflns_number_observed          1721
_reflns_number_total             2185
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            fg1089.cif
_cod_data_source_block           fg1089
_cod_original_sg_symbol_Hall     'P 2y1'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2004499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
I 1 -0.25945(4) -0.25290(11) -0.10592(2) .0586(2) Uani d . I
C10 1 -0.1618(5) -0.5299(12) .2149(3) .0342(12) Uani d . C
O1 1 -.0385(4) -0.5694(12) .2312(2) .0520(11) Uani d . O
C11 1 -0.1991(5) -0.4413(12) .1424(3) .0327(11) Uani d . C
C12 1 -0.1115(5) -0.252(2) .1094(2) .0411(10) Uani d . C
H12 1 -0.0379 -0.1666 .1346 .062 Uiso calc R H
C13 1 -0.1324(6) -0.1904(14) .0399(3) .044(2) Uani d . C
H13 1 -0.0748 -0.0592 .0185 .066 Uiso calc R H
C14 1 -0.2387(6) -0.3227(12) .0018(3) .039(2) Uani d . C
C15 1 -0.3266(6) -0.5137(13) .0333(3) .0417(13) Uani d . C
H15 1 -0.3981 -0.6028 .0073 .063 Uiso calc R H
C16 1 -0.3074(6) -0.5709(13) .1034(3) .0369(12) Uani d . C
H16 1 -0.3672 -0.6973 .1249 .055 Uiso calc R H
N1 1 -0.2672(4) -0.5791(9) .2616(2) .0265(8) Uani d . N
C2 1 -0.3981(5) -0.4389(10) .2677(3) .0285(10) Uani d . C
C3 1 -0.4585(5) -0.5269(10) .3263(3) .0284(10) Uani d . C
C4 1 -0.3680(4) -0.7329(16) .3606(2) .0265(8) Uani d . C
C5 1 -0.3805(5) -0.8958(12) .4202(3) .0296(10) Uani d . C
H5 1 -0.4595 -0.8806 .4473 .044 Uiso calc R H
C6 1 -0.2727(5) -01.0823(11) .4386(3) .0298(10) Uani d . C
C7 1 -0.1548(5) -01.1062(12) .3976(3) .0335(11) Uani d . C
H7 1 -0.0840 -01.2333 .4106 .050 Uiso calc R H
C8 1 -0.1411(5) -0.9454(11) .3384(3) .0327(11) Uani d . C
H8 1 -0.0623 -0.9621 .3111 .049 Uiso calc R H
C9 1 -0.2469(4) -0.7605(16) .3208(2) .0257(8) Uani d . C
C17 1 -0.4516(5) -0.2151(16) .2193(3) .0367(12) Uani d . C
H17A 1 -0.3742 -0.1029 .2040 .055 Uiso calc R H
H17B 1 -0.5167 -0.0963 .2429 .055 Uiso calc R H
H17C 1 -0.4984 -0.3014 .1796 .055 Uiso calc R H
O2 1 -0.2928(3) -01.2360(15) .4984(2) .0431(8) Uani d . O
O3 1 -0.8417(4) -0.4330(11) .3310(3) .0566(12) Uani d D O
H3 1 -0.9067 -0.5016 .3074 .085 Uiso calc RD H
O4 1 -0.7170(4) -0.7347(17) .2708(3) .073(2) Uani d D O
C18 1 -0.5982(5) -0.4272(12) .3520(3) .0333(11) Uani d . C
H18A 1 -0.6042 -0.4750 .4010 .050 Uiso calc R H
H18B 1 -0.6027 -0.2227 .3481 .050 Uiso calc R H
C19 1 -0.7213(5) -0.5514(13) .3133(3) .0381(13) Uani d D C
C20 1 -0.1798(7) -01.4071(15) .5231(3) .049(2) Uani d . C
H20A 1 -0.2068 -01.5056 .5644 .073 Uiso calc R H
H20B 1 -0.0995 -01.2900 .5339 .073 Uiso calc R H
H20C 1 -0.1563 -01.5417 .4878 .073 Uiso calc R 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
O1 C10 N1 121.2(5) yes
O1 C10 C11 118.9(5) yes
N1 C10 C11 119.8(4) yes
C12 C11 C16 118.7(5) yes
C12 C11 C10 118.7(4) yes
C16 C11 C10 122.0(5) yes
C13 C12 C11 120.6(5) yes
C12 C13 C14 120.0(6) yes
C13 C14 C15 120.6(5) yes
C13 C14 I 119.8(4) yes
C15 C14 I 119.6(4) yes
C16 C15 C14 119.4(5) yes
C15 C16 C11 120.7(5) yes
C10 N1 C2 129.1(4) yes
C10 N1 C9 122.1(4) yes
C2 N1 C9 108.1(4) yes
C3 C2 N1 108.9(4) yes
C3 C2 C17 126.6(5) yes
N1 C2 C17 124.3(4) yes
C2 C3 C4 109.0(4) yes
C2 C3 C18 125.5(5) yes
C4 C3 C18 125.5(4) yes
C5 C4 C9 119.2(5) yes
C5 C4 C3 133.3(4) yes
C9 C4 C3 107.5(4) yes
C4 C5 C6 118.8(4) yes
O2 C6 C5 115.2(4) yes
O2 C6 C7 124.2(5) yes
C5 C6 C7 120.6(5) yes
C8 C7 C6 121.3(5) yes
C9 C8 C7 117.9(4) yes
C8 C9 C4 122.3(5) yes
C8 C9 N1 131.1(4) yes
C4 C9 N1 106.5(4) yes
C6 O2 C20 117.2(4) yes
C19 C18 C3 113.6(4) yes
O4 C19 O3 122.0(5) yes
O4 C19 C18 125.9(5) yes
O3 C19 C18 112.2(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I C14 2.094(5) yes
C10 O1 1.218(6) yes
C10 N1 1.383(6) yes
C10 C11 1.483(7) yes
C11 C12 1.388(8) yes
C11 C16 1.396(8) yes
C12 C13 1.372(7) yes
C13 C14 1.378(8) yes
C14 C15 1.381(8) yes
C15 C16 1.377(8) yes
N1 C2 1.418(6) yes
N1 C9 1.431(7) yes
C2 C3 1.343(7) yes
C2 C17 1.487(8) yes
C3 C4 1.444(7) yes
C3 C18 1.507(6) yes
C4 C5 1.384(8) yes
C4 C9 1.407(5) yes
C5 C6 1.389(7) yes
C6 O2 1.375(7) yes
C6 C7 1.393(7) yes
C7 C8 1.376(7) yes
C8 C9 1.367(8) yes
O2 C20 1.414(7) yes
O3 C19 1.328(6) yes
O4 C19 1.191(8) yes
C18 C19 1.487(7) 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
_geom_torsion_publ_flag
C2 N1 C10 C11 -35.0(8) no
N1 C10 C11 C12 144.7(6) no
O1 C10 N1 C2 148.1(6) no
C12 C11 C10 O1 -38.3(8) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 394813
