#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/45/2004542.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_2004542
loop_
_publ_author_name
'Kerrigan, J. E.'
'Powers, J. C.'
'VanDerveer, D.'
_publ_section_title
;
 4-Chloro-7-(iodoacetyl)amino-3-methoxyisocoumarin
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              451
_journal_page_last               453
_journal_paper_doi               10.1107/S0108270195010080
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C12 H9 Cl1 I1 N1 O4'
_chemical_formula_sum            'C12 H9 Cl I N O4'
_chemical_formula_weight         393.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 94.84(5)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   12.165(9)
_cell_length_b                   12.598(11)
_cell_length_c                   8.962(5)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    295
_cell_measurement_theta_max      12.07
_cell_measurement_theta_min      6.25
_cell_volume                     1368.6(17)
_diffrn_measurement_device       'Syntex P2₁'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2580
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        +-3.2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.52
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   'empirical via \y scans'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.66
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.56
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1398
_refine_ls_R_factor_obs          0.050
_refine_ls_shift/esd_max         0.00
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0003F]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.052
_reflns_number_observed          1398
_reflns_number_total             2412
_reflns_observed_criterion       I>2.5\s(I)
_cod_data_source_file            sz1024.cif
_cod_data_source_block           sz1024a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.0003F]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F) +
0.0003F]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1369(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C12 H9 Cl1 I1 N1 O4'
_cod_database_code               2004542
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
C(1) .8395(8) .4222(9) .5038(11) 3.4(5)
O(2) .7498(5) .4228(5) .3983(7) 3.6(3)
C(3) .7046(8) .3319(10) .3417(11) 3.7(5)
C(4) .7417(8) .2358(9) .3821(12) 3.6(5)
C(5) .8770(8) .1305(8) .5475(11) 3.4(5)
C(6) .9645(8) .1293(8) .6552(11) 3.3(5)
C(7) 1.0132(7) .2224(8) .7119(10) 2.7(4)
C(8) .9729(7) .3191(7) .6613(10) 2.8(4)
C(9) .8819(7) .3205(8) .5514(11) 2.9(4)
C(10) .8331(7) .2272(8) .4942(10) 2.7(4)
O(11) .8711(6) .5085(6) .5463(8) 4.8(4)
O(12) .6201(6) .3486(6) .2373(8) 5.1(4)
C(13) .5923(9) .4562(10) .1960(14) 5.6(6)
Cl(14) .67848(22) .12479(22) .3014(3) 4.74(13)
N(15) 1.1021(6) .2112(6) .8251(8) 3.3(4)
C(16) 1.1648(8) .2904(9) .8918(11) 3.0(5)
C(17) 1.2482(7) .2515(8) 1.0146(11) 3.2(5)
I(18) 1.40163(6) .22135(9) .92229(10) 6.57(5)
O(19) 1.1590(6) .3831(6) .8574(9) 4.8(4)
H(5) -.135 .439 -.011 ?
H(6) .010 .428 .183 ?
H(8) .016 .109 .176 ?
H(13A) .427 .010 .217 ?
H(13B) -.340 .500 .149 ?
H(13C) .530 .446 .127 ?
H(15) .102 .356 .386 ?
H(17A) .211 .181 .046 ?
H(17B) .260 .323 .083 ?
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
O(2) C(1) C(9) 116.9(9) yes
O(2) C(1) O(11) 115.1(9) yes
C(9) C(1) O(11) 128.0(9) yes
C(1) O(2) C(3) 121.7(8) yes
O(2) C(3) C(4) 123.4(9) yes
O(2) C(3) O(12) 113.1(10) yes
C(4) C(3) O(12) 123.5(10) yes
C(3) C(4) C(10) 118.9(10) yes
C(7) N(15) C(16) 127.0(8) yes
C(5) C(6) C(7) 121.9(9) yes
N(15) C(16) C(17) 113.5(9) yes
N(15) C(16) O(19) 125.2(9) yes
C(6) C(7) C(8) 119.8(8) yes
C(6) C(7) N(15) 116.8(8) yes
C(8) C(9) C(10) 121.9(9) yes
C(4) C(10) C(5) 123.7(9) yes
C(4) C(10) C(9) 118.2(9) yes
C(5) C(10) C(9) 118.1(8) yes
C(3) O(12) C(13) 118.3(9) yes
C(3) C(4) Cl(14) 119.6(8) yes
C(10) C(4) Cl(14) 121.5(8) yes
C(6) C(5) C(10) 119.9(9) yes
C(17) C(16) O(19) 121.3(9) yes
C(16) C(17) I(18) 109.2(6) yes
C(8) C(7) N(15) 123.4(9) yes
C(7) C(8) C(9) 118.4(8) yes
C(1) C(9) C(8) 117.3(9) yes
C(1) C(9) C(10) 120.8(9) yes
C(6) C(5) H(5) 115.1(10) no
C(10) C(5) H(5) 122.1(10) no
C(5) C(6) H(6) 127.4(11) no
C(7) C(6) H(6) 109.0(10) no
C(7) C(8) H(8) 124.0(9) no
C(9) C(8) H(8) 115.6(9) no
O(12) C(13) H(13A) 118.1(11) no
O(12) C(13) H(13B) 114.0(10) no
O(12) C(13) H(13C) 101.7(11) no
C(7) N(15) H(15) 115.8(8) no
C(16) N(15) H(15) 113.7(8) no
C(16) C(17) H(17A) 101.2(9) no
C(16) C(17) H(17B) 101.2(9) no
I(18) C(17) H(17A) 111.1(8) no
I(18) C(17) H(17B) 106.4(7) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) O(2) 1.385(9) yes
C(1) O(2) 1.382(11) yes
C(1) C(9) 1.433(15) yes
C(1) O(11) 1.204(14) yes
O(2) C(3) 1.350(14) yes
C(3) C(4) 1.331(17) yes
C(3) O(12) 1.347(12) yes
C(4) C(10) 1.439(13) yes
C(4) Cl(14) 1.725(11) yes
C(5) C(6) 1.375(14) yes
C(5) C(10) 1.398(14) yes
C(6) C(7) 1.394(12) yes
C(6) C(7) 1.391(14) yes
C(7) C(8) 1.376(14) yes
C(7) N(15) 1.425(11) yes
C(8) C(9) 1.418(13) yes
C(9) C(10) 1.395(14) yes
O(12) C(13) 1.439(15) yes
N(15) C(16) 1.363(13) yes
C(16) C(17) 1.514(14) yes
C(16) O(19) 1.209(14) yes
C(17) I(18) 2.139(9) yes
C(5) H(5) 1.022(12) no
C(6) H(6) 0.934(11) no
C(8) H(8) 1.054(12) no
C(9) C(10) 1.395(14) no
O(12) C(13) 1.439(15) no
C(13) H(13A) 1.079(15) no
C(13) H(13B) 1.105(14) no
C(13) H(13C) 0.945(12) no
N(15) C(16) 1.363(13) no
N(15) H(15) 1.012(11) no
C(16) C(17) 1.514(14) no
C(16) O(19) 1.209(14) no
C(17) I(18) 2.139(9) no
C(17) H(17A) 1.049(12) no
C(17) H(17B) 1.093(12) no
H(5) C(5) 1.022(12) no
H(6) C(6) 0.934(11) no
H(8) C(8) 1.054(12) no
H(13A) C(13) 1.079(15) no
H(13B) C(13) 1.105(14) no
H(15) N(15) 1.012(11) no
H(17A) C(17) 1.049(12) no
H(17B) C(17) 1.093(12) no
