#------------------------------------------------------------------------------
#$Date: 2020-01-04 06:01:41 +0200 (Sat, 04 Jan 2020) $
#$Revision: 246584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/27/1552745.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_1552745
loop_
_publ_author_name
'Freitag, Matthew'
'DeCicco, Racquel C.'
'Black, Allison'
'Ang, Xiuzhu'
'Young, Christopher N.'
'Resch, Daniel'
'Halada, Gary P.'
'Phillips, Brian L.'
'Goroff, Nancy S.'
_publ_section_title
;
 Polymerization Studies of Diiodohexatriyne and Diiodooctatetrayne
 Cocrystals
;
_journal_issue                   22
_journal_name_full               Macromolecules
_journal_page_first              8563
_journal_paper_doi               10.1021/acs.macromol.9b00960
_journal_volume                  52
_journal_year                    2019
_chemical_formula_moiety         'C6 I2, C8 H13 N2 O'
_chemical_formula_sum            'C14 H13 I2 N2 O'
_chemical_formula_weight         479.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2008-09-02
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_cell_angle_alpha                90.740(5)
_cell_angle_beta                 94.177(4)
_cell_angle_gamma                96.566(5)
_cell_formula_units_Z            2
_cell_length_a                   5.1369(3)
_cell_length_b                   8.3240(6)
_cell_length_c                   19.8365(10)
_cell_measurement_reflns_used    3733
_cell_measurement_theta_max      24.4840
_cell_measurement_theta_min      3.8740
_cell_volume                     840.20(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4962
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.8835
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -22.00  87.00   1.00   19.48    --   10.71  77.00-120.00  109
  2  ω    -40.00  62.00   1.00   19.48    --  -11.57  57.00 120.00  102
  3  ω    -84.00  17.00   1.00   19.48    --  -11.57 -57.00 -30.00  101
  4  ω     34.00  99.00   1.00   19.48    --   10.71 179.00  90.00   65
  5  ω      1.00  70.00   1.00   19.48    --   10.71-132.00 -95.00   69
  6  ω    -86.00  13.00   1.00   19.48    --  -11.57 -37.00  60.00   99
  7  ω    -40.00  62.00   1.00   19.48    --  -11.57  57.00   0.00  102
  8  ω    -71.00 -22.00   1.00   19.48    --  -11.57 132.00 -26.00   49
  9  ω    -99.00 -53.00   1.00   19.48    --  -11.57 179.00 150.00   46
 10  ω    -25.00   0.00   1.00   19.48    --   10.71 -99.00 -60.00   25
 11  ω    -75.00 -26.00   1.00   19.48    --  -11.57 137.00 150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0150622000
_diffrn_orient_matrix_UB_12      0.0757482000
_diffrn_orient_matrix_UB_13      0.0174829000
_diffrn_orient_matrix_UB_21      -0.0011782000
_diffrn_orient_matrix_UB_22      0.0402291000
_diffrn_orient_matrix_UB_23      -0.0313059000
_diffrn_orient_matrix_UB_31      -0.1385591000
_diffrn_orient_matrix_UB_32      -0.0020850000
_diffrn_orient_matrix_UB_33      -0.0005320000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18625
_diffrn_reflns_theta_full        29.8788
_diffrn_reflns_theta_max         29.88
_diffrn_reflns_theta_min         3.25
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.37b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.8935
_exptl_crystal_F_000             448.5159
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.008
_refine_diff_density_max         1.4544
_refine_diff_density_min         -1.0403
_refine_diff_density_rms         0.2449
_refine_ls_d_res_high            0.7133
_refine_ls_d_res_low             6.2771
_refine_ls_goodness_of_fit_ref   1.0279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     171
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0279
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.0070
_refine_ls_shift/su_mean         0.0012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0550P)²+0.5298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1405
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2441
_reflns_number_total             4284
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ma9b00960_si_002.cif
_cod_data_source_block           exp_3425
_cod_depositor_comments
'Adding full bibliography for 1552745--1552747.cif.'
_cod_original_cell_volume        840.22(9)
_cod_database_code               1552745
_chemical_oxdiff_formula         'C28 H26 I4 N4 O2 '
_chemical_oxdiff_usercomment     'C6I2*6MO co-crystal fresh'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of N9, {H12a,H12b} of C12, {H13a,H13b} of C13, {H16a,H16b} of C16, {H15a,
  H15b} of C15, {H17a,H17b} of C17, {H14a,H14b} of C14
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C16(H16a,H16b), C15(H15a,H15b), C17(H17a,
 H17b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.152
_oxdiff_exptl_absorpt_empirical_full_min 0.381
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-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_refinement_flags_posn
I8 I 1.30976(8) 1.16642(6) 0.05201(2) 0.06459(19) Uani 1.000000 .
I1 I 0.04909(10) 0.80255(6) 0.41435(3) 0.0796(2) Uani 1.000000 .
O11 O 0.2097(8) 0.3817(5) 0.4687(2) 0.0614(12) Uani 1.000000 .
N9 N 0.6251(10) 0.3841(6) 0.4364(2) 0.0534(13) Uani 1.000000 .
H9 H 0.7852(10) 0.4273(6) 0.4434(2) 0.0641(15) Uiso 1.000000 R
C10 C 0.4461(11) 0.4343(7) 0.4740(3) 0.0450(13) Uani 1.000000 .
C12 C 0.5623(12) 0.2583(8) 0.3835(3) 0.0570(16) Uani 1.000000 .
H12a H 0.7032(12) 0.1899(8) 0.3840(3) 0.0684(19) Uiso 1.000000 R
H12b H 0.4028(12) 0.1913(8) 0.3931(3) 0.0684(19) Uiso 1.000000 R
C18 C 1.1665(14) 0.6412(9) 0.0764(4) 0.0676(18) Uani 1.000000 .
C13 C 0.5253(11) 0.3279(8) 0.3140(3) 0.0561(15) Uani 1.000000 .
H13a H 0.4342(11) 0.2442(8) 0.2836(3) 0.0673(19) Uiso 1.000000 R
H13b H 0.4138(11) 0.4140(8) 0.3164(3) 0.0673(19) Uiso 1.000000 R
C16 C 0.9901(12) 0.5252(9) 0.1823(3) 0.0619(17) Uani 1.000000 .
H16a H 1.0820(12) 0.6150(9) 0.2093(3) 0.074(2) Uiso 1.000000 R
H16b H 1.1042(12) 0.4402(9) 0.1815(3) 0.074(2) Uiso 1.000000 R
N19 N 1.3425(13) 0.6864(9) 0.0488(4) 0.090(2) Uani 1.000000 .
C15 C 0.7398(12) 0.4626(9) 0.2148(3) 0.0621(17) Uani 1.000000 .
H15a H 0.6319(12) 0.5505(9) 0.2177(3) 0.075(2) Uiso 1.000000 R
H15b H 0.6425(12) 0.3790(9) 0.1855(3) 0.075(2) Uiso 1.000000 R
C7 C 1.0684(14) 1.0753(9) 0.1202(4) 0.0680(18) Uani 1.000000 .
C5 C 0.7440(15) 0.9696(9) 0.2061(4) 0.074(2) Uani 1.000000 .
C17 C 0.9322(14) 0.5802(10) 0.1110(4) 0.073(2) Uani 1.000000 .
H17a H 0.8177(14) 0.6650(10) 0.1123(4) 0.088(2) Uiso 1.000000 R
H17b H 0.8376(14) 0.4902(10) 0.0847(4) 0.088(2) Uiso 1.000000 R
C2 C 0.2669(15) 0.8555(9) 0.3378(4) 0.074(2) Uani 1.000000 .
C6 C 0.9210(14) 1.0258(9) 0.1600(4) 0.0698(19) Uani 1.000000 .
C14 C 0.7817(11) 0.3952(8) 0.2840(3) 0.0588(16) Uani 1.000000 .
H14a H 0.8725(11) 0.4797(8) 0.3140(3) 0.071(2) Uiso 1.000000 R
H14b H 0.8939(11) 0.3094(8) 0.2816(3) 0.071(2) Uiso 1.000000 R
C4 C 0.5880(15) 0.9260(10) 0.2464(4) 0.073(2) Uani 1.000000 .
C3 C 0.4154(14) 0.8843(9) 0.2942(4) 0.0687(19) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 1 1 0.2554
0 1 -28 0.0031
7 -1 -1 0.4015
0 -1 28 0.0046
0 12 3 0.0600
7 -2 -2 0.3990
0 -12 -3 0.0308
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C12 N9 C10 123.0(5) .
N9 C10 O11 124.5(5) .
C10 C10 O11 121.2(6) 2_666
C10 C10 N9 114.3(6) 2_666
C13 C12 N9 112.4(5) .
C17 C18 N19 178.7(8) .
C14 C13 C12 114.4(5) .
C17 C16 C15 111.7(5) .
C14 C15 C16 114.9(5) .
C6 C7 I8 177.7(7) .
C4 C5 C6 177.8(9) .
C16 C17 C18 114.5(6) .
C3 C2 I1 175.0(7) .
C5 C6 C7 178.8(9) .
C15 C14 C13 113.4(5) .
C3 C4 C5 176.8(9) .
C4 C3 C2 176.6(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I8 C7 1.999(7) .
I1 C2 1.976(7) .
O11 C10 1.240(6) .
N9 C10 1.325(7) .
N9 C12 1.466(7) .
C10 C10 1.520(11) 2_666
C12 C13 1.510(9) .
C18 N19 1.121(8) .
C18 C17 1.473(9) .
C13 C14 1.535(7) .
C16 C15 1.522(8) .
C16 C17 1.511(9) .
C15 C14 1.500(9) .
C7 C6 1.179(9) .
C5 C6 1.385(10) .
C5 C4 1.202(10) .
C2 C3 1.202(9) .
C4 C3 1.367(10) .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.2386 1.0887 1.3908 -0.0022 0.0088 1.0000
0.1514 1.3360 -27.8006 -0.3826 0.9239 -0.0090
7.2386 -1.0887 -1.3908 0.0022 -0.0088 -1.0000
-0.1514 -1.3360 27.8006 0.3826 -0.9239 0.0090
0.0660 11.5660 2.6462 0.9234 0.3824 -0.0347
7.2378 -1.7450 -1.8290 -0.0551 -0.0215 -0.9982
-0.2421 -11.5270 -2.6025 -0.9223 -0.3820 0.0590
