data_vmd325
_audit_creation_date               2019-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic         
 '1-butyl-1-methylpiperidinium tetrabromogermanate(II)'
_chemical_formula_moiety           '2(Br), Br2 Ge, 2(C10 H22 N)'
_chemical_formula_sum              'C20 H44 Br4 Ge N2'
_chemical_formula_weight           704.80
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C20 H44 N2 Ge Br4'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Ge' 'Ge' 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     20.0807(7)
_cell_length_b                     8.42480(10)
_cell_length_c                     18.3778(5)
_cell_angle_alpha                  90
_cell_angle_beta                   121.862(4)
_cell_angle_gamma                  90
_cell_volume                       2640.61(16)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7545
_cell_measurement_temperature      122(3)
_cell_measurement_theta_max        30.1690
_cell_measurement_theta_min        2.3830
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      7.222
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.60261
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.23a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear whiteish colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     whiteish
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.773
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1400
_exptl_crystal_preparation         ?
_exptl_crystal_recrystallization_method  'Crystalized from EtOH'
_exptl_crystal_size_max            0.19
_exptl_crystal_size_mid            0.19
_exptl_crystal_size_min            0.19
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0455
_diffrn_reflns_av_unetI/netI       0.0387
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.921
_diffrn_reflns_limit_h_max         28
_diffrn_reflns_limit_h_min         -27
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              20153
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.921
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.911
_diffrn_reflns_theta_min           2.388
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        122(3)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   16.0839
_diffrn_detector_type              Sapphire3
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.921
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -25.00  20.00   1.00   65.44    --  -20.55 -99.00 120.00   45
  2  ω    -25.00  20.00   1.00   65.44    --  -20.55 -99.00  60.00   45
  3  ω    -47.00  40.00   1.00   65.44    --   21.02 -57.00  90.00   87
  4  ω    -17.00  93.00   1.00   65.44    --   21.02  19.00 -90.00  110
  5  ω     34.00  95.00   1.00   65.44    --   21.02 179.00 120.00   61
  6  ω    -25.00  61.00   1.00   65.44    --   21.02 -99.00 -30.00   86
  7  ω    -48.00  50.00   1.00   65.44    --   21.02 -77.00-150.00   98
  8  ω      3.00  42.00   1.00   65.44    --   21.02  57.00 120.00   39
  9  ω      3.00  89.00   1.00   65.44    --   21.02  57.00   0.00   86
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'Xcalibur, Sapphire3'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0058775000
_diffrn_orient_matrix_UB_12        0.0818092000
_diffrn_orient_matrix_UB_13        0.0039589000
_diffrn_orient_matrix_UB_21        -0.0388009000
_diffrn_orient_matrix_UB_22        -0.0164086000
_diffrn_orient_matrix_UB_23        -0.0106838000
_diffrn_orient_matrix_UB_31        0.0137589000
_diffrn_orient_matrix_UB_32        -0.0112923000
_diffrn_orient_matrix_UB_33        0.0439746000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'fine-focus sealed X-ray tube'
_diffrn_source_type                'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3269
_reflns_number_total               3856
_reflns_odcompleteness_completeness  99.97
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       28.22
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.662
_refine_diff_density_min           -0.484
_refine_diff_density_rms           0.110
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.117
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       125
_refine_ls_number_reflns           3856
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0471
_refine_ls_R_factor_gt             0.0342
_refine_ls_restrained_S_all        1.117
_refine_ls_shift/su_max            0.002
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0234P)²+0.5175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0600
_refine_ls_wR_factor_ref           0.0638
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C006(H00C,H00D), C007(H00E,H00F), C008(H00G,H00H), C009(H00I,
 H00J), C00A(H00K,H00L), C00C(H00P,H00Q), C00D(H00R,H00S)
2.b Idealised Me refined as rotating group:
 C00B(H00M,H00N,H00O), C00E(H00T,H00U,H00V)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br01 Br 0.33246(2) 0.54018(3) 0.16608(2) 0.02161(7) Uani 1 1 d . . . . .
 Br02 Br 0.50516(2) 0.34286(3) 0.35594(2) 0.02202(7) Uani 1 1 d . . . . .
 Ge03 Ge 0.500000 0.53130(4) 0.250000 0.01873(9) Uani 1 2 d S T P . .
 N004 N 0.72188(13) 0.4270(2) 0.63103(12) 0.0183(4) Uani 1 1 d . . . . .
 C005 C 0.68993(15) 0.5928(3) 0.62343(15) 0.0182(5) Uani 1 1 d . . . . .
 H00A H 0.732306 0.667896 0.640543 0.022 Uiso 1 1 calc R . . . .
 H00B H 0.672684 0.602954 0.663560 0.022 Uiso 1 1 calc R . . . .
 C006 C 0.62242(16) 0.6388(3) 0.53504(16) 0.0228(6) Uani 1 1 d . . . . .
 H00C H 0.576925 0.573981 0.519784 0.027 Uiso 1 1 calc R . . . .
 H00D H 0.636865 0.620654 0.493004 0.027 Uiso 1 1 calc R . . . .
 C007 C 0.75045(16) 0.3969(3) 0.57075(16) 0.0208(5) Uani 1 1 d . . . . .
 H00E H 0.766565 0.286913 0.575678 0.025 Uiso 1 1 calc R . . . .
 H00F H 0.707644 0.414619 0.512271 0.025 Uiso 1 1 calc R . . . .
 C008 C 0.85925(17) 0.5060(3) 0.74445(17) 0.0238(6) Uani 1 1 d . . . . .
 H00G H 0.902193 0.480716 0.801821 0.029 Uiso 1 1 calc R . . . .
 H00H H 0.844833 0.616040 0.744088 0.029 Uiso 1 1 calc R . . . .
 C009 C 0.81834(17) 0.5031(3) 0.58969(17) 0.0245(6) Uani 1 1 d . . . . .
 H00I H 0.800964 0.612744 0.579469 0.029 Uiso 1 1 calc R . . . .
 H00J H 0.836036 0.476898 0.551191 0.029 Uiso 1 1 calc R . . . .
 C00A C 0.79016(16) 0.4011(3) 0.72195(15) 0.0219(6) Uani 1 1 d . . . . .
 H00K H 0.773033 0.421946 0.761480 0.026 Uiso 1 1 calc R . . . .
 H00L H 0.806452 0.290890 0.728728 0.026 Uiso 1 1 calc R . . . .
 C00B C 0.53455(17) 0.8664(4) 0.44853(18) 0.0316(7) Uani 1 1 d . . . . .
 H00M H 0.544084 0.835884 0.404478 0.047 Uiso 1 1 calc GR . . . .
 H00N H 0.529283 0.979668 0.448316 0.047 Uiso 1 1 calc GR . . . .
 H00O H 0.487160 0.817143 0.438067 0.047 Uiso 1 1 calc GR . . . .
 C00C C 0.88618(18) 0.4850(4) 0.68173(18) 0.0299(6) Uani 1 1 d . . . . .
 H00P H 0.926099 0.563347 0.693660 0.036 Uiso 1 1 calc R . . . .
 H00Q H 0.909325 0.380556 0.689342 0.036 Uiso 1 1 calc R . . . .
 C00D C 0.60273(16) 0.8134(3) 0.53502(16) 0.0231(6) Uani 1 1 d . . . . .
 H00R H 0.589696 0.830890 0.578253 0.028 Uiso 1 1 calc R . . . .
 H00S H 0.648425 0.877249 0.549980 0.028 Uiso 1 1 calc R . . . .
 C00E C 0.65994(18) 0.3079(3) 0.61255(18) 0.0287(7) Uani 1 1 d . . . . .
 H00T H 0.639149 0.328606 0.648161 0.043 Uiso 1 1 calc GR . . . .
 H00U H 0.682181 0.203292 0.624180 0.043 Uiso 1 1 calc GR . . . .
 H00V H 0.618624 0.315232 0.553400 0.043 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br02 Ge03 2.4716(3) . ?
 N004 C005 1.512(3) . ?
 N004 C007 1.514(3) . ?
 N004 C00A 1.517(3) . ?
 N004 C00E 1.491(3) . ?
 C005 C006 1.517(3) . ?
 C006 C00D 1.523(3) . ?
 C007 C009 1.510(4) . ?
 C008 C00A 1.507(4) . ?
 C008 C00C 1.520(3) . ?
 C009 C00C 1.519(4) . ?
 C00B C00D 1.518(4) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 Br02 Ge03 Br02 100.068(17) . 2_655 ?
 C005 N004 C007 113.17(18) . . ?
 C005 N004 C00A 109.14(17) . . ?
 C007 N004 C00A 108.1(2) . . ?
 C00E N004 C005 109.8(2) . . ?
 C00E N004 C007 108.25(19) . . ?
 C00E N004 C00A 108.31(19) . . ?
 N004 C005 C006 115.51(19) . . ?
 C005 C006 C00D 109.4(2) . . ?
 C009 C007 N004 112.1(2) . . ?
 C00A C008 C00C 111.6(2) . . ?
 C007 C009 C00C 111.5(2) . . ?
 C008 C00A N004 112.54(19) . . ?
 C009 C00C C008 111.3(2) . . ?
 C00B C00D C006 112.0(2) . . ?

_olex2_submission_original_sample_id  a
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.735
_oxdiff_exptl_absorpt_empirical_full_min  0.824
