#------------------------------------------------------------------------------
#$Date: 2019-09-28 02:36:20 +0200 (Sat 28 de Sep de 2019) $
#$Revision: 218890 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/42/7234217.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_7234217
loop_
_publ_author_name
'Torubaev, Yury'
'Skabitskiy, Ivan V.'
_publ_section_title
;
 The Energy Frameworks of Aufbau Synthon Modules in 4-Cyanopyridine
 Co-crystals.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01174A
_journal_year                    2019
_chemical_formula_moiety         'C I, C6 H4 N2'
_chemical_formula_sum            'C7 H4 I N2'
_chemical_formula_weight         243.02
_chemical_name_systematic        '4-cyanopyridine 1,2-diiodoethene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-18 deposited with the CCDC.    2019-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.154(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2421(3)
_cell_length_b                   7.0061(6)
_cell_length_c                   27.717(2)
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      3.00
_cell_volume                     822.52(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.634
_diffrn_reflns_theta_min         2.944
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.819
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0934 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.7156.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_recrystallization_method 'solution in heptane cooling at -10C'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0246P)²+1.5771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1671
_reflns_number_total             2285
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL 1_a.res in P2(1)/n
    1.res
    created by SHELXL-2018/3 at 16:57:49 on 18-Jul-2019
REM Old TITL 1 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.109, Rweak 0.021, Alpha 0.025, Orientation as input
REM Formula found by SHELXT: C7 N2 I
CELL 0.71073 4.2421 7.0061 27.7172 90 93.154 90
ZERR 4 0.0003 0.0006 0.0022 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H I N
UNIT 28 16 4 8

L.S. 16
PLAN  20
SIZE 0.04 0.04 0.2
TEMP 22.85
BOND $H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.024600    1.577100
FVAR       0.50194
I2    3    0.766153    0.718289    0.447531    11.00000    0.05471    0.06089 =
         0.06489   -0.00731   -0.00358   -0.00847
C2    1    0.947781    0.935472    0.489022    11.00000    0.05165    0.06791 =
         0.05861   -0.00707    0.00103   -0.01036
N1    4    0.486301    0.436730    0.386450    11.00000    0.06945    0.07024 =
         0.06630   -0.00728   -0.00042   -0.00782
N2    4   -0.184892   -0.095626    0.288764    11.00000    0.13670    0.11373 =
         0.08919   -0.02673   -0.00619   -0.03582
C3    1   -0.041986    0.020252    0.307933    11.00000    0.07485    0.08995 =
         0.07179   -0.01662    0.00097   -0.00731
C4    1    0.139632    0.163105    0.334978    11.00000    0.06286    0.06192 =
         0.05117   -0.00922    0.00797   -0.00329
C5    1    0.190611    0.339280    0.314909    11.00000    0.09119    0.07732 =
         0.05842    0.00852   -0.01487    0.00046
AFIX  43
HB    2    0.109456    0.369037    0.283970    11.00000   -1.20000
AFIX   0
C6    1    0.367969    0.472019    0.342432    11.00000    0.09918    0.07090 =
         0.08143    0.01881   -0.00574   -0.01163
AFIX  43
HC    2    0.404301    0.591159    0.329024    11.00000   -1.20000
AFIX   0
C7    1    0.431882    0.266638    0.404579    11.00000    0.07522    0.08673 =
         0.05105    0.00276   -0.00701   -0.00387
AFIX  43
HA    2    0.511880    0.240069    0.435769    11.00000   -1.20000
AFIX   0
C8    1    0.263354    0.126396    0.379901    11.00000    0.07283    0.06661 =
         0.06441    0.00969   -0.00207   -0.01056
AFIX  43
H     2    0.234988    0.007636    0.394010    11.00000   -1.20000
AFIX   0
HKLF 4




REM  1_a.res in P2(1)/n
REM wR2 = 0.0947, GooF = S = 1.179, Restrained GooF = 1.179 for all data
REM R1 = 0.0543 for 1671 Fo > 4sig(Fo) and 0.0848 for all 2285 data
REM 91 parameters refined using 0 restraints

END  
     
WGHT      0.0246      1.5747 

REM Highest difference peak  0.637,  deepest hole -0.948,  1-sigma level  0.098
Q1    1   0.6694  0.7774  0.4251  11.00000  0.05    0.64
Q2    1   0.9054  0.8004  0.4575  11.00000  0.05    0.55
Q3    1   0.5419  0.7124  0.4443  11.00000  0.05    0.54
Q4    1   0.7397  0.5954  0.4427  11.00000  0.05    0.52
Q5    1   0.9932  0.7001  0.4418  11.00000  0.05    0.36
Q6    1  -0.1856  0.0626  0.2849  11.00000  0.05    0.34
Q7    1   0.7352  0.7371  0.4773  11.00000  0.05    0.33
Q8    1   0.3228  0.1768  0.3426  11.00000  0.05    0.32
Q9    1   0.0199  0.4446  0.2820  11.00000  0.05    0.29
Q10   1  -0.1336 -0.3082  0.2386  11.00000  0.05    0.29
Q11   1   0.2009  0.2116  0.3195  11.00000  0.05    0.29
Q12   1   0.2836  0.3981  0.3413  11.00000  0.05    0.28
Q13   1   0.3163  0.7801  0.3576  11.00000  0.05    0.27
Q14   1   0.2616  0.2922  0.4791  11.00000  0.05    0.26
Q15   1   0.9661  0.6602  0.4267  11.00000  0.05    0.26
Q16   1   0.3400  0.2532  0.2813  11.00000  0.05    0.25
Q17   1  -0.0084  0.4293  0.3556  11.00000  0.05    0.25
Q18   1  -0.2022 -0.2262  0.2805  11.00000  0.05    0.24
Q19   1   0.1130  0.6726  0.3571  11.00000  0.05    0.23
Q20   1   0.7155  0.3730  0.4222  11.00000  0.05    0.23

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0543 for 1671 Fo > 4sig(Fo) and 0.0848 for all 15905 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.64, deepest hole -0.95
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0848
  REM R1_gt = 0.0543
  REM wR_ref = 0.0947
  REM GOOF = 1.179
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 15905
  REM Reflections_gt = 1671
  REM Parameters = n/a
  REM Hole = -0.95
  REM Peak = 0.64
  REM Flack = n/a

  
;
_cod_data_source_file            c9ce01174a2.cif
_cod_data_source_block           1_CCDC3
_cod_database_code               7234217
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.516
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(HB), C6(HC), C7(HA), C8(H)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
I2 I 0.76615(9) 0.71829(6) 0.44753(2) 0.06042(16) Uani 1 1 d .
C2 C 0.9478(13) 0.9355(9) 0.4890(2) 0.0595(14) Uani 1 1 d .
N1 N 0.4863(12) 0.4367(8) 0.38645(19) 0.0688(13) Uani 1 1 d .
N2 N -0.1849(18) -0.0956(11) 0.2888(2) 0.114(2) Uani 1 1 d .
C3 C -0.0420(16) 0.0203(11) 0.3079(2) 0.0790(19) Uani 1 1 d .
C4 C 0.1396(14) 0.1631(9) 0.3350(2) 0.0585(14) Uani 1 1 d .
C5 C 0.1906(17) 0.3393(10) 0.3149(2) 0.0763(18) Uani 1 1 d .
HB H 0.109456 0.369037 0.283970 0.092 Uiso 1 1 calc R
C6 C 0.3680(17) 0.4720(10) 0.3424(3) 0.084(2) Uani 1 1 d .
HC H 0.404301 0.591159 0.329024 0.101 Uiso 1 1 calc R
C7 C 0.4319(16) 0.2666(10) 0.4046(2) 0.0714(17) Uani 1 1 d .
HA H 0.511880 0.240069 0.435769 0.086 Uiso 1 1 calc R
C8 C 0.2634(14) 0.1264(9) 0.3799(2) 0.0682(16) Uani 1 1 d .
H H 0.234988 0.007636 0.394010 0.082 Uiso 1 1 calc R
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
I2 0.0547(2) 0.0609(3) 0.0649(3) -0.00731(19) -0.00358(17) -0.00847(18)
C2 0.052(3) 0.068(4) 0.059(4) -0.007(3) 0.001(3) -0.010(3)
N1 0.069(3) 0.070(3) 0.066(3) -0.007(3) 0.000(3) -0.008(3)
N2 0.137(6) 0.114(6) 0.089(5) -0.027(4) -0.006(4) -0.036(5)
C3 0.075(4) 0.090(5) 0.072(4) -0.017(4) 0.001(4) -0.007(4)
C4 0.063(3) 0.062(4) 0.051(3) -0.009(3) 0.008(3) -0.003(3)
C5 0.091(5) 0.077(4) 0.058(4) 0.009(3) -0.015(3) 0.000(4)
C6 0.099(5) 0.071(4) 0.081(5) 0.019(4) -0.006(4) -0.012(4)
C7 0.075(4) 0.087(5) 0.051(3) 0.003(3) -0.007(3) -0.004(4)
C8 0.073(4) 0.067(4) 0.064(4) 0.010(3) -0.002(3) -0.011(3)
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'
I I -0.4742 1.8119 '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'
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
C2 C2 I2 177.1(8) 3_776
C6 N1 C7 117.2(6) .
N2 C3 C4 176.8(8) .
C5 C4 C3 120.1(6) .
C8 C4 C3 121.0(6) .
C8 C4 C5 118.8(6) .
C4 C5 HB 121.0 .
C4 C5 C6 117.9(6) .
C6 C5 HB 121.0 .
N1 C6 C5 123.2(6) .
N1 C6 HC 118.4 .
C5 C6 HC 118.4 .
N1 C7 HA 118.2 .
N1 C7 C8 123.6(6) .
C8 C7 HA 118.2 .
C4 C8 C7 119.2(6) .
C4 C8 H 120.4 .
C7 C8 H 120.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I2 C2 2.033(5) .
C2 C2 1.164(11) 3_776
N1 C6 1.317(8) .
N1 C7 1.319(8) .
N2 C3 1.128(8) .
C3 C4 1.447(9) .
C4 C5 1.376(9) .
C4 C8 1.349(8) .
C5 HB 0.9300 .
C5 C6 1.396(9) .
C6 HC 0.9300 .
C7 HA 0.9300 .
C7 C8 1.375(9) .
C8 H 0.9300 .
