Solid state halogen bonded networks vs. dynamic assemblies in solution: explaining N⋯X interactions of multivalent building blocks
Tero, Tiia-Riikka; Salorinne, Kirsi; Malola, Sami; Häkkinen, Hannu; Nissinen, Maija; CrystEngComm 17 (2015) 8231–; doi:10.1039/C5CE01144B

data_7235876
_publ_section_title
;
 Solid state halogen bonded networks vs. dynamic assemblies in solution:
 explaining N&#x22EF;X interactions of multivalent building blocks
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              8231
_journal_paper_doi               10.1039/C5CE01144B
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C60 H60 N4 O8, 3(C H Cl3)'
_chemical_formula_sum            'C63 H60 Cl9 D3 N4 O8'
_chemical_formula_weight         1326.24
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-01-22 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.199(4)
_cell_angle_beta                 94.142(3)
_cell_angle_gamma                110.327(4)
_cell_formula_units_Z            2
_cell_length_a                   13.5142(6)
_cell_length_b                   14.6744(7)
_cell_length_c                   17.3471(7)
_cell_measurement_reflns_used    5782
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.4850
_cell_measurement_theta_min      2.6080
_cell_volume                     3192.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details
;
  1 omega  -60.00  -35.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.9470 -178.0000 -150.0000 25

  2 omega   21.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408  -99.0000  -60.0000 44

  3 omega  -12.00   52.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408  -99.0000  120.0000 64

  4 omega  -20.00   16.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408  -99.0000   30.0000 36

  5 omega   36.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408  -99.0000 -180.0000 29

  6 omega   -7.00   56.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408   77.0000   60.0000 63

  7 omega  -42.00   38.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408  -57.0000  150.0000 80

  8 omega  -21.00   96.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0408   19.0000  -30.0000 117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0494785000
_diffrn_orient_matrix_UB_12      0.0393806000
_diffrn_orient_matrix_UB_13      0.0043468000
_diffrn_orient_matrix_UB_21      0.0158324000
_diffrn_orient_matrix_UB_22      -0.0168947000
_diffrn_orient_matrix_UB_23      0.0341384000
_diffrn_orient_matrix_UB_31      0.0217506000
_diffrn_orient_matrix_UB_32      -0.0293601000
_diffrn_orient_matrix_UB_33      -0.0228573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31467
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1372
_exptl_crystal_size_max          0.3486
_exptl_crystal_size_mid          0.2352
_exptl_crystal_size_min          0.1686
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0043(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         17182
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1888
_refine_ls_R_factor_gt           0.0995
_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^)+(0.1480P)^2^+1.8200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2709
_refine_ls_wR_factor_ref         0.3386
_reflns_number_gt                7597
_reflns_number_total             17182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01144b2.cif
_cod_data_source_block           2-CHCl3
_cod_original_cell_volume        3192.8(2)
_cod_database_code               7235876
_chemical_oxdiff_formula         'C60 H60 O4 N4'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {D20A,D20B,D201} of C201, All C(H,H) groups
 At 1.5 times of:
  {H29A,H29B,H29C} of C29, {H30A,H30B,H30C} of C30, {H31A,H31B,H31C} of C31,
  {H32A,H32B,H32C} of C32, {H33A,H33B,H33C} of C33, {H34A,H34B,H34C} of C34,
  {H35A,H35B,H35C} of C35, {H36A,H36B,H36C} of C36
2. Restrained distances
 C201-Cl4C = C201-Cl5C
 1.79 with sigma of 0.02
 Cl7B-C301
 1.79 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl4A \\sim Cl4C \\sim Cl5A \\sim Cl5C \\sim Cl6A \\sim Cl6C: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(Cl7B) = Uanis(Cl7A)
4. Others
 1*[Sof(D201)+Sof(Cl4A)+Sof(Cl5A)+Sof(Cl6A)]+1*[Sof(D20A)+Sof(Cl4B)+Sof(Cl5B)+
 Sof(Cl6B)]+1*[Sof(D20B)+Sof(Cl4C)+Sof(Cl5C)+Sof(Cl6C)]=1 with esd of 0.001
 Sof(D201)=Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=FVAR(1)
 Sof(D20A)=Sof(Cl4B)=Sof(Cl5B)=Sof(Cl6B)=FVAR(2)
 Sof(D20B)=Sof(Cl4C)=Sof(Cl5C)=Sof(Cl6C)=FVAR(3)
 Fixed Sof: Cl7A(0.5) Cl7B(0.5) D301(0.5) D30D(0.5)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28), C101(D101), C301(D301), C301(D30D),
 C201(D20A), C201(D20B), C201(D201)
5.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C51(H51A,H51B), C61(H61A,H61B), C71(H71A,H71B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26),
 C43(H43), C44(H44), C45(H45), C46(H46), C53(H53), C54(H54), C55(H55), C56(H56),
  C63(H63), C64(H64), C65(H65), C66(H66), C73(H73), C74(H74), C75(H75), C76(H76)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C)
;
_ins_header
;
TITL 2-CHCl3 in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073  13.514237  14.674417  17.347099  95.1994  94.1424 110.3270
ZERR    2.00   0.000550   0.000740   0.000733   0.0038   0.0034   0.0041
LATT  1
SFAC C H N O
UNIT 120.00 120.00 8.00 8.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'