#------------------------------------------------------------------------------
#$Date: 2018-09-04 11:41:10 +0300 (Tue, 04 Sep 2018) $
#$Revision: 210387 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/23/4512315.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4512315
loop_
_publ_author_name
'Kim, Yejin'
'Mckinley, Emma J.'
'Christensen, Kirsten E.'
'Rees, Nicholas H.'
'Thompson, Amber L.'
_publ_section_title
;
 Toward the Understanding of Modulation in Molecular Materials:
 Barluenga's Reagent and its Analogues.
;
_journal_coden_ASTM              CGDEFU
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6294
_journal_page_last               6301
_journal_paper_doi               10.1021/cg500983s
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C10 H10 I N2, Cl O4'
_chemical_formula_sum            'C10 H10 Cl I N2 O4'
_chemical_formula_weight         384.56
_chemical_melting_point          ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             14-06-09
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 113.742(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1261(2)
_cell_length_b                   15.9708(2)
_cell_length_c                   14.7929(2)
_cell_measurement_reflns_used    12444
_cell_measurement_temperature    30
_cell_measurement_theta_max      32
_cell_measurement_theta_min      2
_cell_volume                     2622.39(8)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution
'Refinement from previously reported BF4 analogue'
_diffrn_ambient_temperature      30
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device       'CrystalLogic Kappa (3 circle)'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34698
_diffrn_reflns_theta_full        27.973
_diffrn_reflns_theta_max         31.787
_diffrn_reflns_theta_min         1.789
_diffrn_source                   Synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.654
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.79
_refine_diff_density_min         -0.66
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         7727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.0013524
_refine_ls_shift/su_mean         0.0000357
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.152E+04 0.251E+04 0.159E+04 691. 164. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0612
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0612
_reflns_limit_h_max              16
_reflns_limit_h_min              -18
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                7031
_reflns_number_total             9190
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.79
_oxford_diffrn_Wilson_scale      0.25
_oxford_refine_ls_r_factor_ref   0.0294
_oxford_refine_ls_scale          2.126(6)
_oxford_reflns_number_all        7727
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 027yk13-30K
_cod_data_source_file            cg500983s_si_002.cif
_cod_data_source_block           IPy2ClO4-30K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary'
value 'Other' changed to 'other' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4512310--4512328.cif.
;
_cod_original_formula_sum        'C10 H10 Cl1 I1 N2 O4'
_cod_database_code               4512315
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
I1 I 0.0000 0.0000 0.0000 0.0094 1.0000 Uani S
N1 N -0.06553(13) 0.11528(10) 0.05066(11) 0.0125 1.0000 Uani .
C11 C -0.09032(16) 0.18447(12) -0.00573(14) 0.0158 1.0000 Uani .
C12 C -0.13192(18) 0.25676(12) 0.02077(17) 0.0191 1.0000 Uani .
C13 C -0.14770(18) 0.25770(12) 0.10905(17) 0.0199 1.0000 Uani .
C14 C -0.12257(17) 0.18577(13) 0.16639(15) 0.0191 1.0000 Uani .
C15 C -0.08090(16) 0.11511(12) 0.13585(14) 0.0156 1.0000 Uani .
I2 I 0.5000 0.0000 0.5000 0.0109 1.0000 Uani S
N2 N 0.57209(14) 0.09516(10) 0.42426(11) 0.0128 1.0000 Uani .
C21 C 0.61395(16) 0.16937(11) 0.46766(13) 0.0135 1.0000 Uani .
C22 C 0.65504(16) 0.22969(12) 0.42178(14) 0.0144 1.0000 Uani .
C23 C 0.65380(16) 0.21267(11) 0.32895(13) 0.0146 1.0000 Uani .
C24 C 0.61178(16) 0.13545(12) 0.28562(13) 0.0151 1.0000 Uani .
C25 C 0.57153(16) 0.07780(12) 0.33517(13) 0.0148 1.0000 Uani .
I3 I 1.005980(10) 0.245124(7) 0.494451(8) 0.0106 1.0000 Uani .
N3 N 1.08210(13) 0.34882(10) 0.43320(11) 0.0132 1.0000 Uani .
C31 C 1.10870(16) 0.42361(12) 0.47840(13) 0.0147 1.0000 Uani .
C32 C 1.15268(16) 0.48853(12) 0.44036(14) 0.0161 1.0000 Uani .
C33 C 1.16854(16) 0.47564(12) 0.35347(14) 0.0155 1.0000 Uani .
C34 C 1.14045(16) 0.39811(12) 0.30739(13) 0.0148 1.0000 Uani .
C35 C 1.09730(16) 0.33553(12) 0.34951(13) 0.0141 1.0000 Uani .
N4 N 0.93109(13) 0.13760(10) 0.55105(11) 0.0132 1.0000 Uani .
C41 C 0.89080(16) 0.07015(12) 0.49233(14) 0.0160 1.0000 Uani .
C42 C 0.84848(18) 0.00032(12) 0.52360(16) 0.0200 1.0000 Uani .
C43 C 0.84736(18) 0.00053(13) 0.61747(17) 0.0217 1.0000 Uani .
C44 C 0.88779(17) 0.07140(14) 0.67600(15) 0.0208 1.0000 Uani .
C45 C 0.92982(16) 0.13938(13) 0.64115(13) 0.0160 1.0000 Uani .
Cl1 Cl 0.76497(4) 0.30116(3) 0.71682(3) 0.0130 1.0000 Uani .
O1 O 0.85516(14) 0.24757(12) 0.78454(12) 0.0303 1.0000 Uani .
O2 O 0.79862(13) 0.32365(9) 0.63659(10) 0.0179 1.0000 Uani .
O3 O 0.7552(2) 0.37537(11) 0.76835(14) 0.0383 1.0000 Uani .
O4 O 0.65099(13) 0.25860(10) 0.67858(11) 0.0195 1.0000 Uani .
Cl2 Cl 0.73376(4) 0.44371(3) 0.27539(3) 0.0123 1.0000 Uani .
O5 O 0.68637(12) 0.41661(9) 0.34580(10) 0.0159 1.0000 Uani .
O6 O 0.66954(14) 0.51771(11) 0.22469(12) 0.0244 1.0000 Uani .
O8 O 0.71796(15) 0.37815(11) 0.20411(12) 0.0276 1.0000 Uani .
O7 O 0.86004(12) 0.46335(9) 0.32553(11) 0.0181 1.0000 Uani .
H111 H -0.0796 0.1829 -0.0644 0.0196 1.0000 Uiso R
H121 H -0.1498 0.3036 -0.0207 0.0239 1.0000 Uiso R
H131 H -0.1757 0.3067 0.1290 0.0244 1.0000 Uiso R
H141 H -0.1335 0.1846 0.2254 0.0238 1.0000 Uiso R
H151 H -0.0648 0.0662 0.1743 0.0191 1.0000 Uiso R
H211 H 0.6138 0.1796 0.5298 0.0158 1.0000 Uiso R
H221 H 0.6821 0.2812 0.4523 0.0170 1.0000 Uiso R
H231 H 0.6797 0.2530 0.2968 0.0182 1.0000 Uiso R
H241 H 0.6089 0.1224 0.2232 0.0183 1.0000 Uiso R
H251 H 0.5436 0.0261 0.3076 0.0179 1.0000 Uiso R
H311 H 1.0953 0.4306 0.5355 0.0181 1.0000 Uiso R
H321 H 1.1711 0.5398 0.4731 0.0198 1.0000 Uiso R
H331 H 1.1971 0.5182 0.3263 0.0197 1.0000 Uiso R
H341 H 1.1499 0.3870 0.2491 0.0187 1.0000 Uiso R
H351 H 1.0777 0.2826 0.3208 0.0177 1.0000 Uiso R
H411 H 0.8917 0.0710 0.4298 0.0190 1.0000 Uiso R
H421 H 0.8197 -0.0458 0.4816 0.0240 1.0000 Uiso R
H431 H 0.8182 -0.0458 0.6404 0.0265 1.0000 Uiso R
H441 H 0.8873 0.0751 0.7388 0.0260 1.0000 Uiso R
H451 H 0.9574 0.1863 0.6795 0.0191 1.0000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156
;
 International Tables Vol C 4.2.6.8 and 6.1.1.4 and 
 D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030
;
 International Tables Vol C 4.2.6.8 and 6.1.1.4 and 
 D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
Cl 0.1250 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574
;
 International Tables Vol C 4.2.6.8 and 6.1.1.4 and 
 D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
I -0.7740 1.7190 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712
;
 International Tables Vol C 4.2.6.8 and 6.1.1.4 and 
 D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
N 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290
;
 International Tables Vol C 4.2.6.8 and 6.1.1.4 and 
 D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
O 0.0070 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508
;
 International Tables Vol C 4.2.6.8 and 6.1.1.4 and 
 D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 2_555 I1 N1 179.995 yes
I1 . N1 C11 119.13(12) yes
I1 . N1 C15 120.71(13) yes
C11 . N1 C15 120.15(16) yes
N1 . C11 C12 121.88(19) yes
N1 . C11 H111 118.5 no
C12 . C11 H111 119.6 no
C11 . C12 C13 118.65(19) yes
C11 . C12 H121 119.9 no
C13 . C12 H121 121.5 no
C12 . C13 C14 118.99(18) yes
C12 . C13 H131 120.1 no
C14 . C13 H131 120.9 no
C13 . C14 C15 119.66(19) yes
C13 . C14 H141 120.6 no
C15 . C14 H141 119.7 no
C14 . C15 N1 120.67(18) yes
C14 . C15 H151 119.7 no
N1 . C15 H151 119.6 no
N2 2_656 I2 N2 179.995 yes
I2 . N2 C21 120.14(12) yes
I2 . N2 C25 119.77(12) yes
C21 . N2 C25 120.09(16) yes
N2 . C21 C22 121.39(17) yes
N2 . C21 H211 118.2 no
C22 . C21 H211 120.4 no
C21 . C22 C23 119.01(17) yes
C21 . C22 H221 120.3 no
C23 . C22 H221 120.7 no
C22 . C23 C24 118.96(17) yes
C22 . C23 H231 119.9 no
C24 . C23 H231 121.1 no
C23 . C24 C25 119.28(17) yes
C23 . C24 H241 121.1 no
C25 . C24 H241 119.6 no
C24 . C25 N2 121.26(17) yes
C24 . C25 H251 120.5 no
N2 . C25 H251 118.3 no
N3 . I3 N4 177.52(6) yes
I3 . N3 C31 120.53(12) yes
I3 . N3 C35 119.05(12) yes
C31 . N3 C35 120.40(16) yes
N3 . C31 C32 121.20(17) yes
N3 . C31 H311 117.7 no
C32 . C31 H311 121.1 no
C31 . C32 C33 118.97(18) yes
C31 . C32 H321 119.8 no
C33 . C32 H321 121.2 no
C32 . C33 C34 119.25(17) yes
C32 . C33 H331 120.6 no
C34 . C33 H331 120.2 no
C33 . C34 C35 118.99(17) yes
C33 . C34 H341 121.8 no
C35 . C34 H341 119.2 no
C34 . C35 N3 121.20(17) yes
C34 . C35 H351 121.4 no
N3 . C35 H351 117.4 no
I3 . N4 C41 117.74(12) yes
I3 . N4 C45 121.39(13) yes
C41 . N4 C45 120.84(17) yes
N4 . C41 C42 121.11(18) yes
N4 . C41 H411 119.0 no
C42 . C41 H411 119.9 no
C41 . C42 C43 119.01(19) yes
C41 . C42 H421 120.2 no
C43 . C42 H421 120.8 no
C42 . C43 C44 118.71(18) yes
C42 . C43 H431 120.9 no
C44 . C43 H431 120.4 no
C43 . C44 C45 119.83(19) yes
C43 . C44 H441 122.0 no
C45 . C44 H441 118.2 no
C44 . C45 N4 120.49(19) yes
C44 . C45 H451 120.5 no
N4 . C45 H451 119.0 no
O1 . Cl1 O2 109.51(10) yes
O1 . Cl1 O3 108.91(12) yes
O2 . Cl1 O3 109.90(9) yes
O1 . Cl1 O4 109.61(10) yes
O2 . Cl1 O4 109.81(9) yes
O3 . Cl1 O4 109.08(11) yes
O5 . Cl2 O6 109.34(9) yes
O5 . Cl2 O8 109.59(9) yes
O6 . Cl2 O8 109.17(11) yes
O5 . Cl2 O7 110.06(8) yes
O6 . Cl2 O7 109.11(9) yes
O8 . Cl2 O7 109.56(9) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 N1 2_555 2.2499(15) yes
I1 N1 . 2.2499(15) yes
N1 C11 . 1.344(2) yes
N1 C15 . 1.346(2) yes
C11 C12 . 1.379(3) yes
C11 H111 . 0.928 no
C12 C13 . 1.394(3) yes
C12 H121 . 0.936 no
C13 C14 . 1.387(3) yes
C13 H131 . 0.946 no
C14 C15 . 1.384(3) yes
C14 H141 . 0.934 no
C15 H151 . 0.940 no
I2 N2 2_656 2.2623(16) yes
I2 N2 . 2.2623(16) yes
N2 C21 . 1.346(2) yes
N2 C25 . 1.344(2) yes
C21 C22 . 1.382(3) yes
C21 H211 . 0.934 no
C22 C23 . 1.394(3) yes
C22 H221 . 0.932 no
C23 C24 . 1.389(3) yes
C23 H231 . 0.927 no
C24 C25 . 1.383(3) yes
C24 H241 . 0.934 no
C25 H251 . 0.922 no
I3 N3 . 2.2559(16) yes
I3 N4 . 2.2555(15) yes
N3 C31 . 1.343(2) yes
N3 C35 . 1.340(2) yes
C31 C32 . 1.385(3) yes
C31 H311 . 0.929 no
C32 C33 . 1.389(3) yes
C32 H321 . 0.932 no
C33 C34 . 1.388(3) yes
C33 H331 . 0.925 no
C34 C35 . 1.387(2) yes
C34 H341 . 0.931 no
C35 H351 . 0.933 no
N4 C41 . 1.346(2) yes
N4 C45 . 1.339(2) yes
C41 C42 . 1.383(3) yes
C41 H411 . 0.930 no
C42 C43 . 1.394(3) yes
C42 H421 . 0.937 no
C43 C44 . 1.389(3) yes
C43 H431 . 0.941 no
C44 C45 . 1.384(3) yes
C44 H441 . 0.934 no
C45 H451 . 0.918 no
Cl1 O1 . 1.4317(16) yes
Cl1 O2 . 1.4471(14) yes
Cl1 O3 . 1.4397(16) yes
Cl1 O4 . 1.4361(14) yes
Cl2 O5 . 1.4437(13) yes
Cl2 O6 . 1.4476(15) yes
Cl2 O8 . 1.4430(15) yes
Cl2 O7 . 1.4418(14) yes
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 H111 O1 1_454 140.82 0.928 2.295 3.070(3) yes
C13 H131 O8 1_455 153.68 0.946 2.314 3.190(3) yes
C15 H151 O6 3_545 126.88 0.940 2.445 3.101(3) yes
C21 H211 O4 . 156.01 0.934 2.417 3.292(3) yes
C23 H231 O8 . 170.10 0.927 2.569 3.487(3) yes
C31 H311 O7 2_766 139.01 0.929 2.548 3.306(3) yes
C33 H331 O2 2_766 127.26 0.925 2.581 3.226(3) yes
C33 H331 O3 2_766 171.06 0.925 2.416 3.333(3) yes
C34 H341 O4 4_554 125.09 0.931 2.552 3.179(3) yes
C41 H411 O6 3_645 150.23 0.930 2.265 3.107(3) yes
C43 H431 O3 3_646 160.77 0.941 2.272 3.176(3) yes
C45 H451 O1 . 123.14 0.918 2.541 3.139(3) yes
