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_7211200
_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, C23 H31 N O'
_chemical_formula_sum            'C29 H32 F4 I N O'
_chemical_formula_weight         613.46
_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             2013-02-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                107.3165(15)
_cell_angle_beta                 94.6772(17)
_cell_angle_gamma                92.7169(16)
_cell_formula_units_Z            2
_cell_length_a                   5.47910(12)
_cell_length_b                   13.3643(2)
_cell_length_c                   18.9794(3)
_cell_measurement_reflns_used    14147
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      32.1374
_cell_measurement_theta_min      3.0500
_cell_volume                     1318.59(4)
_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      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9922
_diffrn_measurement_details
;
  1 omega  -42.00   48.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735  -57.0000  -30.0000 90

  2 omega   -7.00   72.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735 -107.0000  -64.0000 79

  3 omega   28.00   73.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735 -108.0000  115.0000 45

  4 omega  -20.00   53.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735  -99.0000 -150.0000 73

  5 omega  -15.00  100.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735   19.0000  150.0000 115

  6 omega    6.00   95.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735   57.0000   30.0000 89

  7 omega   -3.00   97.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735   77.0000 -180.0000 100

  8 omega   35.00  100.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735  178.0000 -180.0000 65

  9 omega    6.00   95.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735   57.0000  -60.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0453935000
_diffrn_orient_matrix_UB_12      0.0035361000
_diffrn_orient_matrix_UB_13      0.0368112000
_diffrn_orient_matrix_UB_21      -0.1215891000
_diffrn_orient_matrix_UB_22      0.0018874000
_diffrn_orient_matrix_UB_23      0.0103583000
_diffrn_orient_matrix_UB_31      -0.0110777000
_diffrn_orient_matrix_UB_32      -0.0556081000
_diffrn_orient_matrix_UB_33      -0.0092546000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24377
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.21
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.907
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_recrystallization_method DCM
_exptl_crystal_size_max          0.2109
_exptl_crystal_size_mid          0.1062
_exptl_crystal_size_min          0.0988
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         8462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+0.3796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                7729
_reflns_number_total             8462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41454j.txt
_cod_data_source_block           dwb1311
_cod_database_code               7211200
_chemical_oxdiff_formula         'C29 H32 F4 I1 N1 O1'
_chemical_oxdiff_usercomment     'Linda E216D'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H23A,H23B} of C23, H19 of C19, H10 of C10, {H25A,H25B} of C25, {H26A,H26B}
  of C26, {H21A,H21B} of C21, H15 of C15, {H24A,H24B} of C24, H11 of C11, {H22A,
  H22B} of C22, {H27A,H27B} of C27, H13 of C13, H18 of C18, H16 of C16, {H20A,
  H20B} of C20, {H28A,H28B} of C28, H12 of C12, H7 of C7, H8 of C8, H4 of C4
 At 1.5 times of:
  {H29A,H29B,H29C} of C29
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), C27(H27A,H27B), C28(H28A,H28B)
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:
 C29(H29A,H29B,H29C)
;