#------------------------------------------------------------------------------
#$Date: 2019-11-17 05:15:10 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228066 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/22/7122275.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7122275
loop_
_publ_author_name
'Majumdar, Moumita'
'Raut, Ravindra K.'
'Sahoo, Padmini'
'Kumar, Vikas'
_publ_section_title
;
 Bis(chlorogermyliumylidene) and its significant role in elusive reductive
 cyclization.
;
_journal_issue                   77
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10839
_journal_page_last               10842
_journal_paper_doi               10.1039/c8cc06067c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C16 H22 N4, C F3 S O3, C F3 S O3'
_chemical_formula_sum            'C18 H22 F6 N4 O6 S2'
_chemical_formula_weight         568.51
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-21 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.836(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8024(17)
_cell_length_b                   17.854(3)
_cell_length_c                   12.5096(19)
_cell_measurement_reflns_used    9306
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.84
_cell_measurement_theta_min      3.86
_cell_volume                     2411.2(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 'CMOS-Photon 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19759
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.858
_diffrn_reflns_theta_max         66.858
_diffrn_reflns_theta_min         4.349
_diffrn_source                   'Fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.833
_exptl_absorpt_correction_T_max  0.797
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS;Universitat Gottingen,1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0591P)²+4.4591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3869
_reflns_number_total             4241
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc06067c2.cif
_cod_data_source_block           compound4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7122274--7122277.cif.
;
_cod_original_cell_volume        2411.2(6)
_cod_database_code               7122275
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S2 S 0.47767(6) 0.29933(4) 0.65457(5) 0.02399(18) Uani 1 1 d . .
S1 S 0.30078(6) 0.11564(4) 0.06007(6) 0.0292(2) Uani 1 1 d . .
O3 O 0.33629(19) 0.09634(11) 0.18129(17) 0.0319(5) Uani 1 1 d . .
O4 O 0.43908(18) 0.35916(11) 0.56913(16) 0.0284(4) Uani 1 1 d . .
O5 O 0.50548(19) 0.22998(11) 0.60972(17) 0.0328(5) Uani 1 1 d . .
F3 F 0.51841(19) 0.17190(12) 0.1122(2) 0.0565(6) Uani 1 1 d . .
O6 O 0.5647(2) 0.32034(13) 0.76866(17) 0.0398(5) Uani 1 1 d . .
F2 F 0.5090(2) 0.05237(12) 0.08638(18) 0.0550(6) Uani 1 1 d . .
F4 F 0.24432(19) 0.26298(14) 0.5676(2) 0.0612(6) Uani 1 1 d . .
N4 N 0.1654(2) 0.38926(13) 0.00479(19) 0.0251(5) Uani 1 1 d . .
O2 O 0.2540(2) 0.19045(14) 0.0293(2) 0.0458(6) Uani 1 1 d . .
F6 F 0.3001(2) 0.33772(17) 0.7164(2) 0.0707(7) Uani 1 1 d . .
F1 F 0.4350(2) 0.12467(16) -0.06228(19) 0.0661(7) Uani 1 1 d . .
N2 N 0.2627(2) 0.30900(12) 0.18887(19) 0.0227(5) Uani 1 1 d . .
H2A H 0.1830 0.2963 0.1582 0.027 Uiso 1 1 calc R U
H2B H 0.2924 0.3008 0.1348 0.027 Uiso 1 1 calc R U
N3 N 0.4843(2) 0.35743(13) 0.36953(19) 0.0247(5) Uani 1 1 d . .
H3A H 0.5649 0.3674 0.3957 0.030 Uiso 1 1 calc R U
H3B H 0.4616 0.3654 0.4284 0.030 Uiso 1 1 calc R U
N1 N 0.4373(2) 0.35148(13) 0.1081(2) 0.0262(5) Uani 1 1 d . .
O1 O 0.2271(2) 0.06032(16) -0.0212(2) 0.0547(7) Uani 1 1 d . .
F5 F 0.3490(3) 0.22130(18) 0.7417(3) 0.0890(9) Uani 1 1 d . .
C5 C 0.2055(2) 0.43276(15) 0.0997(2) 0.0203(5) Uani 1 1 d . .
C3 C 0.4149(2) 0.41330(14) 0.2722(2) 0.0200(5) Uani 1 1 d . .
C10 C 0.4744(2) 0.40898(15) 0.1834(2) 0.0225(6) Uani 1 1 d . .
C6 C 0.1868(2) 0.50978(15) 0.0947(2) 0.0235(6) Uani 1 1 d . .
H6 H 0.2125 0.5384 0.1626 0.028 Uiso 1 1 calc R U
C4 C 0.2729(2) 0.39167(13) 0.2172(2) 0.0194(5) Uani 1 1 d . .
C9 C 0.1087(2) 0.42231(17) -0.0998(2) 0.0283(6) Uani 1 1 d . .
H9 H 0.0806 0.3923 -0.1662 0.034 Uiso 1 1 calc R U
C16 C 0.4365(2) 0.48921(15) 0.3334(2) 0.0257(6) Uani 1 1 d . .
H16A H 0.3919 0.4913 0.3827 0.039 Uiso 1 1 calc R U
H16B H 0.4079 0.5283 0.2759 0.039 Uiso 1 1 calc R U
H16C H 0.5234 0.4957 0.3800 0.039 Uiso 1 1 calc R U
C2 C 0.4662(3) 0.27693(16) 0.3389(2) 0.0298(6) Uani 1 1 d . .
H2C H 0.5106 0.2467 0.4076 0.036 Uiso 1 1 calc R U
H2D H 0.4983 0.2655 0.2806 0.036 Uiso 1 1 calc R U
C1 C 0.3299(3) 0.25923(16) 0.2916(2) 0.0301(6) Uani 1 1 d . .
H1A H 0.3162 0.2071 0.2677 0.036 Uiso 1 1 calc R U
H1B H 0.2989 0.2674 0.3516 0.036 Uiso 1 1 calc R U
C15 C 0.2076(2) 0.40646(15) 0.2991(2) 0.0233(6) Uani 1 1 d . .
H15A H 0.1289 0.3814 0.2697 0.035 Uiso 1 1 calc R U
H15B H 0.1951 0.4593 0.3031 0.035 Uiso 1 1 calc R U
H15C H 0.2578 0.3879 0.3758 0.035 Uiso 1 1 calc R U
C7 C 0.1285(2) 0.54289(16) -0.0150(3) 0.0278(6) Uani 1 1 d . .
H7 H 0.1157 0.5944 -0.0216 0.033 Uiso 1 1 calc R U
C8 C 0.0902(2) 0.49858(17) -0.1136(2) 0.0289(6) Uani 1 1 d . .
H8 H 0.0526 0.5196 -0.1877 0.035 Uiso 1 1 calc R U
C14 C 0.4871(3) 0.34404(17) 0.0291(3) 0.0331(7) Uani 1 1 d . .
H14 H 0.4609 0.3046 -0.0238 0.040 Uiso 1 1 calc R U
C13 C 0.5751(3) 0.3924(2) 0.0234(3) 0.0417(8) Uani 1 1 d . .
H13 H 0.6080 0.3857 -0.0321 0.050 Uiso 1 1 calc R U
C11 C 0.5625(3) 0.4597(2) 0.1832(3) 0.0395(8) Uani 1 1 d . .
H11 H 0.5872 0.4990 0.2366 0.047 Uiso 1 1 calc R U
C18 C 0.4489(3) 0.11581(19) 0.0467(3) 0.0373(7) Uani 1 1 d . .
C12 C 0.6134(3) 0.4507(2) 0.1014(3) 0.0509(9) Uani 1 1 d . .
H12 H 0.6731 0.4841 0.0995 0.061 Uiso 1 1 calc R U
C17 C 0.3344(3) 0.2785(2) 0.6712(3) 0.0476(9) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O6 S2 O4 115.31(13)
O6 S2 O5 115.22(13)
O4 S2 O5 113.38(12)
O6 S2 C17 105.34(16)
O4 S2 C17 101.86(15)
O5 S2 C17 103.60(16)
O1 S1 O2 113.17(16)
O1 S1 O3 114.64(15)
O2 S1 O3 114.85(13)
O1 S1 C18 105.43(16)
O2 S1 C18 104.67(15)
O3 S1 C18 102.40(13)
C5 N4 C9 118.0(2)
C1 N2 C4 114.5(2)
C1 N2 H2A 108.6
C4 N2 H2A 108.6
C1 N2 H2B 108.6
C4 N2 H2B 108.6
H2A N2 H2B 107.6
C2 N3 C3 116.9(2)
C2 N3 H3A 108.1
C3 N3 H3A 108.1
C2 N3 H3B 108.1
C3 N3 H3B 108.1
H3A N3 H3B 107.3
C10 N1 C14 118.4(3)
N4 C5 C6 122.8(2)
N4 C5 C4 115.5(2)
C6 C5 C4 121.6(2)
C16 C3 N3 104.6(2)
C16 C3 C10 112.0(2)
N3 C3 C10 106.8(2)
C16 C3 C4 111.6(2)
N3 C3 C4 108.6(2)
C10 C3 C4 112.8(2)
N1 C10 C11 122.2(3)
N1 C10 C3 115.5(2)
C11 C10 C3 122.2(2)
C5 C6 C7 118.0(3)
C5 C6 H6 121.0
C7 C6 H6 121.0
N2 C4 C15 108.1(2)
N2 C4 C5 106.22(19)
C15 C4 C5 110.4(2)
N2 C4 C3 108.1(2)
C15 C4 C3 113.5(2)
C5 C4 C3 110.2(2)
N4 C9 C8 123.2(3)
N4 C9 H9 118.4
C8 C9 H9 118.4
C3 C16 H16A 109.5
C3 C16 H16B 109.5
H16A C16 H16B 109.5
C3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N3 C2 C1 108.9(2)
N3 C2 H2C 109.9
C1 C2 H2C 109.9
N3 C2 H2D 109.9
C1 C2 H2D 109.9
H2C C2 H2D 108.3
N2 C1 C2 108.9(2)
N2 C1 H1A 109.9
C2 C1 H1A 109.9
N2 C1 H1B 109.9
C2 C1 H1B 109.9
H1A C1 H1B 108.3
C4 C15 H15A 109.5
C4 C15 H15B 109.5
H15A C15 H15B 109.5
C4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C8 C7 C6 119.4(3)
C8 C7 H7 120.3
C6 C7 H7 120.3
C7 C8 C9 118.4(3)
C7 C8 H8 120.8
C9 C8 H8 120.8
N1 C14 C13 122.7(3)
N1 C14 H14 118.7
C13 C14 H14 118.7
C12 C13 C14 118.6(3)
C12 C13 H13 120.7
C14 C13 H13 120.7
C10 C11 C12 118.4(3)
C10 C11 H11 120.8
C12 C11 H11 120.8
F1 C18 F2 108.4(3)
F1 C18 F3 109.4(3)
F2 C18 F3 107.9(3)
F1 C18 S1 111.9(2)
F2 C18 S1 110.7(2)
F3 C18 S1 108.5(2)
C13 C12 C11 119.6(3)
C13 C12 H12 120.2
C11 C12 H12 120.2
F5 C17 F4 109.2(3)
F5 C17 F6 108.2(3)
F4 C17 F6 108.5(3)
F5 C17 S2 111.0(3)
F4 C17 S2 110.1(2)
F6 C17 S2 109.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 O6 1.431(2)
S2 O4 1.448(2)
S2 O5 1.451(2)
S2 C17 1.824(4)
S1 O1 1.432(2)
S1 O2 1.437(2)
S1 O3 1.442(2)
S1 C18 1.822(3)
F3 C18 1.343(4)
F2 C18 1.322(4)
F4 C17 1.332(4)
N4 C5 1.335(3)
N4 C9 1.342(4)
F6 C17 1.337(5)
F1 C18 1.316(4)
N2 C1 1.498(3)
N2 C4 1.511(3)
N2 H2A 0.8900
N2 H2B 0.8900
N3 C2 1.481(4)
N3 C3 1.531(3)
N3 H3A 0.8900
N3 H3B 0.8900
N1 C10 1.342(3)
N1 C14 1.344(4)
F5 C17 1.314(5)
C5 C6 1.390(4)
C5 C4 1.544(3)
C3 C16 1.527(4)
C3 C10 1.537(4)
C3 C4 1.581(3)
C10 C11 1.379(4)
C6 C7 1.394(4)
C6 H6 0.9300
C4 C15 1.534(4)
C9 C8 1.379(4)
C9 H9 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C2 C1 1.506(4)
C2 H2C 0.9700
C2 H2D 0.9700
C1 H1A 0.9700
C1 H1B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C7 C8 1.379(4)
C7 H7 0.9300
C8 H8 0.9300
C14 C13 1.375(5)
C14 H14 0.9300
C13 C12 1.373(5)
C13 H13 0.9300
C11 C12 1.390(5)
C11 H11 0.9300
C12 H12 0.9300
