Subtle C‒H···Hal (Hal = Cl, Br) Bonding as Predominant Synthon in the Assembly of Supramolecular Architectures Based on Luminescent Tin(IV) Complexes. Crystallography, Hirshfeld Surfaces, DFT Calculations, and Fluorescence
Guzmán-Percástegui, Edmundo; Alvarado-Rodríguez, José G.; Cruz-Borbolla, Julián; Andrade-López, Noemí; Vázquez-García, Rosa A.; Nava-Galindo, Rigo N.; Pandiyan, Thangarasu; Crystal Growth & Design 14 (2014) 3742–; doi:10.1021/cg401818k

data_4511534
_publ_contact_author             'Jose Guadalupe Alvarado Rodriguez'
_publ_section_title
;
 Subtle C--H&#x00B7;&#x00B7;&#x00B7;Hal (Hal = Cl, Br) Bonding as
 Predominant Synthon in the Assembly of Supramolecular Architectures Based
 on Luminescent Tin(IV) Complexes. Crystallography, Hirshfeld Surfaces,
 DFT Calculations, and Fluorescence
;
_journal_issue                   8
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              3742
_journal_paper_doi               10.1021/cg401818k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C16 H18 Cl2 N2 O Sn'
_chemical_formula_sum            'C16 H18 Cl2 N2 O Sn'
_chemical_formula_weight         443.91
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.701(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.6097(7)
_cell_length_b                   12.5384(3)
_cell_length_c                   17.9005(8)
_cell_measurement_reflns_used    14492
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.2060
_cell_measurement_theta_min      3.0348
_cell_volume                     3499.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -67.00   42.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -       12.2125  -77.0000  -60.0000 109

  2 omega  -62.00    6.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -       12.2125  -57.0000 -180.0000 68

  3 omega  -99.00  -53.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -      -10.7281  178.0000   90.0000 46

  4 omega  -25.00   31.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -      -10.7281  -99.0000  120.0000 56

  5 omega  -25.00    4.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -       12.2125  -99.0000  150.0000 29

  6 omega  -17.00   86.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -       12.2125   57.0000   60.0000 103

  7 omega  -21.00   91.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -       12.2125   77.0000  -90.0000 112

  8 omega   35.00  102.00   1.0000   11.6600
omega____ theta____ kappa____ phi______ frames
    -       12.2125  178.0000  150.0000 67
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0417234000
_diffrn_orient_matrix_UB_12      0.0222922000
_diffrn_orient_matrix_UB_13      -0.0167163000
_diffrn_orient_matrix_UB_21      -0.0134778000
_diffrn_orient_matrix_UB_22      -0.0324626000
_diffrn_orient_matrix_UB_23      -0.0364257000
_diffrn_orient_matrix_UB_31      -0.0121218000
_diffrn_orient_matrix_UB_32      -0.0406442000
_diffrn_orient_matrix_UB_33      0.0199049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50955
_diffrn_reflns_theta_full        26.26
_diffrn_reflns_theta_max         26.26
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
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_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.3073
_exptl_crystal_size_mid          0.1686
_exptl_crystal_size_min          0.1386
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         7065
_refine_ls_number_restraints     388
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0231P)^2^+3.4258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                5219
_reflns_number_total             7065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401818k_si_001.cif
_cod_data_source_block           3_[Sn(PyNO)(n-Bu)Cl2]
_cod_depositor_comments
'Adding full bibliography for 4511532--4511537.cif.'
_cod_original_cell_volume        3499.4(2)
_cod_database_code               4511534
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.21
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H30C,H30D} of C30A, {H31C,H31D} of C31A, {H29E,H29F} of C29B, {H29C,H29D}
  of C29A, {H30A,H30B} of C30, H26 of C26, H22 of C22, {H29A,H29B} of C29, H25
  of C25, H24 of C24, H20 of C20, H19 of C19, {H31A,H31B} of C31, H27 of C27,
  {H14C,H14D} of C14A, {H15C,H15D} of C15A, H17 of C17, H18 of C18, {H31E,H31F}
  of C31B, {H30E,H30F} of C30B, {H15A,H15B} of C15, {H13C,H13D} of C13A, {H14A,
  H14B} of C14, H9 of C9, H10 of C10, H11 of C11, {H13A,H13B} of C13, H8 of C8,
  H4 of C4, H1 of C1, H6 of C6, H3 of C3, H2 of C2
 At 1.5 times of:
  {H32D,H32E,H32F} of C32A, {H32A,H32B,H32C} of C32, {H16D,H16E,H16F} of C16A,
   {H32G,H32H,H32I} of C32B, {H16A,H16B,H16C} of C16
2. Restrained distances
 C13-C14
 1.54 with sigma of 0.01
 C29-C30
 1.54 with sigma of 0.01
 C13-Sn1 ~ C13A-Sn1
 with sigma of 0.01
 C13-C14 ~ C14-C15 ~ C15-C16
 with sigma of 0.01
 C13-C15 ~ C14-C16
 with sigma of 0.01
 C29-Sn2 ~ C29A-Sn2 ~ C29B-Sn2
 with sigma of 0.01
 C29-C30 ~ C30-C31 ~ C31-C32
 with sigma of 0.01
 C29-C31 ~ C30-C32
 with sigma of 0.01
 C29A-C31A ~ C30A-C32A
 with sigma of 0.01
3. Rigid bond restraints
 C13, C14, C15, C16, C13A, C14A, C15A, C16A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C29, C30, C31, C32, C29A, C30A, C31A, C32A, C29B, C30B, C31B, C32B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C13 ~ C14 ~ C15 ~ C16 ~ C13A ~ C14A ~ C15A ~ C16A: within 1.7A with 
sigma of 0.01 and sigma for terminal atoms of 0.02
C29 ~ C30 ~ C31 ~ C32 ~ C29A ~ C30A ~ C31A ~ C32A ~ C29B ~ C30B ~ C31B ~ C32B: 
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Same fragment restrains
{C13, C14, C15, C16}
as
{C13A, C14A, C15A, C16A}
{C29, C30, C31, C32}
as
{C29A, C30A, C31A, C32A}
{C29, C30, C31, C32}
as
{C29B, C30B, C31B, C32B}
6. Others
 1*[Sof(C29)+Sof(H29A)+Sof(H29B)+Sof(C30)+Sof(H30A)+Sof(H30B)+Sof(C31)+
 Sof(H31A)+Sof(H31B)+Sof(C32)+Sof(H32A)+Sof(H32B)+Sof(H32C)]+1*[Sof(C29A)+
 Sof(H29C)+Sof(H29D)+Sof(C30A)+Sof(H30C)+Sof(H30D)+Sof(C31A)+Sof(H31C)+
 Sof(H31D)+Sof(C32A)+Sof(H32D)+Sof(H32E)+Sof(H32F)]+1*[Sof(C29B)+Sof(H29E)+
 Sof(H29F)+Sof(C30B)+Sof(H30E)+Sof(H30F)+Sof(C31B)+Sof(H31E)+Sof(H31F)+
 Sof(C32B)+Sof(H32G)+Sof(H32H)+Sof(H32I)]=1 with esd of 0.0001
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=
 Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)
 Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=
 Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)
 Sof(C29B)=Sof(H29E)=Sof(H29F)=Sof(C30B)=Sof(H30E)=Sof(H30F)=Sof(C31B)=
 Sof(H31E)=Sof(H31F)=Sof(C32B)=Sof(H32G)=Sof(H32H)=Sof(H32I)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=1-Sof(H13A)=1-Sof(H13A)=1-
 Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)=1-
 Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)=1-Sof(H13A)
7.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C13A(H13C,H13D), C14A(H14C,
 H14D), C15A(H15C,H15D), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
 C29A(H29C,H29D), C30A(H30C,H30D), C31A(H31C,H31D), C29B(H29E,H29F), C30B(H30E,
 H30F), C31B(H31E,H31F)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27)
7.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F), C32(H32A,H32B,H32C), C32A(H32D,
 H32E,H32F), C32B(H32G,H32H,H32I)
;