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_7211199
_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         'C6 H F4 I, C21 H27 N O'
_chemical_formula_sum            'C27 H28 F4 I N O'
_chemical_formula_weight         585.40
_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             2013-07-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Nov  5 2012 18:25:38, GUI svn.r4372)
;
_cell_angle_alpha                94.229(2)
_cell_angle_beta                 94.338(3)
_cell_angle_gamma                95.863(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4342(2)
_cell_length_b                   11.9349(4)
_cell_length_c                   19.0791(5)
_cell_measurement_reflns_used    7504
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.0119
_cell_measurement_theta_min      3.2168
_cell_volume                     1223.26(7)
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details
;
  1 omega  -42.00   38.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -57.0000   30.0000 80

  2 omega   71.00   97.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -178.0000    0.0000 26

  3 omega   -9.00   68.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000  -30.0000 77

  4 omega   23.00   67.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000 -180.0000 44

  5 omega  -36.00   18.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -57.0000 -120.0000 54

  6 omega   40.00   66.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000   60.0000 26

  7 omega  -17.00   99.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   19.0000 -150.0000 116
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0434092000
_diffrn_orient_matrix_UB_12      0.0175405000
_diffrn_orient_matrix_UB_13      -0.0330069000
_diffrn_orient_matrix_UB_21      0.0669107000
_diffrn_orient_matrix_UB_22      0.0540502000
_diffrn_orient_matrix_UB_23      0.0087153000
_diffrn_orient_matrix_UB_31      0.1047694000
_diffrn_orient_matrix_UB_32      -0.0190897000
_diffrn_orient_matrix_UB_33      -0.0153001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12406
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.776
_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            'dull light yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.3585
_exptl_crystal_size_mid          0.0557
_exptl_crystal_size_min          0.0396
_refine_diff_density_max         1.217
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         7188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.1352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                6440
_reflns_number_total             7188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41454j.txt
_cod_data_source_block           dwb1250
_cod_original_cell_volume        1223.27(7)
_cod_database_code               7211199
_chemical_oxdiff_formula         'C27 H28 F4 I1 N1 O1'
_chemical_oxdiff_usercomment     'Linda - E186I'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.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)
2.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)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;