1 : 1 and 2 : 1 co-crystals of alkoxystilbazoles with tetrafluoroiodobenzenes: halogen bonding, a rare Carene–H⋯N hydrogen bond and unsymmetric iodine⋯pyridine interactions
Präsang, Carsten; McAllister, Linda J.; Whitwood, Adrian C.; Bruce, Duncan W.; CrystEngComm 15 (2013) 8947–; doi:10.1039/c3ce41454j

data_7211201
_publ_section_title
;
 1&#x2009;:&#x2009;1 and 2&#x2009;:&#x2009;1 co-crystals of
 alkoxystilbazoles with tetrafluoroiodobenzenes: halogen bonding, a rare
 Carene--H&#x22EF;N hydrogen bond and unsymmetric iodine&#x22EF;pyridine
 interactions
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              8947
_journal_paper_doi               10.1039/c3ce41454j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         '2(C21 H27 N O), C6 H F4 I'
_chemical_formula_sum            'C48 H55 F4 I N2 O2'
_chemical_formula_weight         894.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                67.842(4)
_cell_angle_beta                 87.532(3)
_cell_angle_gamma                72.143(3)
_cell_formula_units_Z            1
_cell_length_a                   7.6705(2)
_cell_length_b                   11.9764(5)
_cell_length_c                   13.1845(5)
_cell_measurement_reflns_used    6938
_cell_measurement_temperature    109.95(10)
_cell_measurement_theta_max      28.4939
_cell_measurement_theta_min      2.8542
_cell_volume                     1064.08(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      109.95(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9900
_diffrn_measurement_details
;
  1 omega   -8.00   18.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.9830  -99.0000 -180.0000 26

  2 omega  -52.00   35.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330  -57.0000   60.0000 87

  3 omega  -52.00    7.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330  -57.0000 -180.0000 59

  4 omega  -52.00   34.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330  -57.0000  -60.0000 86

  5 omega   35.00   73.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330  178.0000  -30.0000 38

  6 omega   -2.00   86.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330   57.0000  -30.0000 88

  7 omega  -20.00   59.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330  -99.0000 -180.0000 79

  8 omega   31.00   70.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330 -117.0000   -5.0000 39

  9 omega   -4.00   86.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330   57.0000   90.0000 90

 10 omega   -3.00   86.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2330   57.0000 -150.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0373253000
_diffrn_orient_matrix_UB_12      -0.0378385000
_diffrn_orient_matrix_UB_13      0.0451511000
_diffrn_orient_matrix_UB_21      -0.0418846000
_diffrn_orient_matrix_UB_22      -0.0176616000
_diffrn_orient_matrix_UB_23      -0.0359542000
_diffrn_orient_matrix_UB_31      0.0797201000
_diffrn_orient_matrix_UB_32      -0.0528430000
_diffrn_orient_matrix_UB_33      0.0081184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14829
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         2.86
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.3355
_exptl_crystal_size_mid          0.0943
_exptl_crystal_size_min          0.0324
_refine_diff_density_max         1.402
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.5304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                4040
_reflns_number_total             4722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41454j.txt
_cod_data_source_block           dwb1254
_cod_original_cell_volume        1064.09(7)
_cod_database_code               7211201
_chemical_oxdiff_formula         'C48 H55 F4 I1 N2 O2'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H20A,H20B} of C20, H19 of C19, H18 of C18, H16 of C16, H15 of C15, H13 of
  C13, H12 of C12, H11 of C11, H10 of C10, H8 of C8, {H24A,H24B} of C24, {H25A,
  H25B} of C25, {H26A,H26B} of C26, H7 of C7, H4 of C4, {H21A,H21B} of C21,
  {H22A,H22B} of C22, {H23A,H23B} of C23
 At 1.5 times of:
  {H27A,H27B,H27C} of C27
2. Uiso/Uaniso restraints and constraints
Uanis(C2) ~ Ueq, Uanis(C6) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
3. Others
 Fixed Sof: C1(0.5) C2(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5) C6(0.5) F3(0.5)
 F1(0.5) F4(0.5) F2(0.5) I1(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;