#------------------------------------------------------------------------------
#$Date: 2019-11-26 10:03:08 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/33/4133396.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_4133396
loop_
_publ_author_name
'de la Vega-Hernández, Karen'
'Romain, Elise'
'Coffinet, Anais'
'Bijouard, Kajetan'
'Gontard, Geoffrey'
'Chemla, Fabrice'
'Ferreira, Franck'
'Jackowski, Olivier'
'Perez-Luna, Alejandro'
_publ_section_title
;
 Radical Germylzincation of α-Heteroatom-Substituted Alkynes.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17632
_journal_page_last               17642
_journal_paper_doi               10.1021/jacs.8b09851
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C39 H33 Ge N O2'
_chemical_formula_sum            'C39 H33 Ge N O2'
_chemical_formula_weight         620.25
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.862(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0689(2)
_cell_length_b                   17.7248(3)
_cell_length_c                   16.4657(3)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      2.30
_cell_volume                     3230.11(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37208
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.577
_diffrn_reflns_theta_min         1.688
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         9896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0476P)²+1.1848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                7797
_reflns_number_total             9896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b09851_si_002.cif
_cod_data_source_block           Compound_40
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4133396
_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
Ge1 Ge 0.20066(2) 0.19678(2) 0.62431(2) 0.02677(6) Uani 1 1 d . .
O1 O 0.29711(13) 0.42195(7) 0.43841(7) 0.0397(3) Uani 1 1 d . .
O2 O 0.35197(12) 0.52527(7) 0.50816(8) 0.0378(3) Uani 1 1 d . .
N1 N 0.31660(12) 0.42074(7) 0.57755(8) 0.0263(3) Uani 1 1 d . .
C1 C 0.20600(14) 0.30684(9) 0.61088(9) 0.0261(3) Uani 1 1 d . .
C2 C 0.30835(14) 0.34039(9) 0.58594(9) 0.0260(3) Uani 1 1 d . .
C3 C 0.31988(14) 0.45182(9) 0.50249(10) 0.0290(3) Uani 1 1 d . .
C4 C 0.36771(19) 0.54530(11) 0.59221(12) 0.0421(4) Uani 1 1 d . .
H4A H 0.3018 0.5791 0.6095 0.050 Uiso 1 1 calc R U
H4B H 0.4457 0.5716 0.6008 0.050 Uiso 1 1 calc R U
C5 C 0.36549(16) 0.47152(10) 0.64104(10) 0.0317(3) Uani 1 1 d . .
C6 C 0.49191(19) 0.44809(13) 0.66848(13) 0.0481(5) Uani 1 1 d . .
H6A H 0.5215 0.4829 0.7105 0.072 Uiso 1 1 calc R U
H6B H 0.4895 0.3968 0.6906 0.072 Uiso 1 1 calc R U
H6C H 0.5462 0.4495 0.6220 0.072 Uiso 1 1 calc R U
C7 C 0.2812(2) 0.47717(14) 0.71289(13) 0.0551(6) Uani 1 1 d . .
H7A H 0.3163 0.5112 0.7538 0.083 Uiso 1 1 calc R U
H7B H 0.2028 0.4969 0.6944 0.083 Uiso 1 1 calc R U
H7C H 0.2702 0.4270 0.7368 0.083 Uiso 1 1 calc R U
C8 C 0.41327(15) 0.29931(9) 0.56131(10) 0.0299(3) Uani 1 1 d . .
C9 C 0.49794(15) 0.26739(10) 0.53298(10) 0.0323(3) Uani 1 1 d . .
C10 C 0.59683(16) 0.22880(10) 0.49630(10) 0.0342(4) Uani 1 1 d . .
C11 C 0.5778(2) 0.16097(13) 0.45590(14) 0.0522(5) Uani 1 1 d . .
H11 H 0.4994 0.1391 0.4536 0.063 Uiso 1 1 calc R U
C12 C 0.6747(3) 0.12526(16) 0.41879(16) 0.0683(7) Uani 1 1 d . .
H12 H 0.6615 0.0790 0.3908 0.082 Uiso 1 1 calc R U
C13 C 0.7875(2) 0.15530(17) 0.42191(16) 0.0686(8) Uani 1 1 d . .
H13 H 0.8527 0.1299 0.3970 0.082 Uiso 1 1 calc R U
C14 C 0.8068(2) 0.22267(18) 0.46132(15) 0.0621(7) Uani 1 1 d . .
H14 H 0.8856 0.2439 0.4631 0.074 Uiso 1 1 calc R U
C15 C 0.71222(18) 0.26004(13) 0.49865(13) 0.0456(5) Uani 1 1 d . .
H15 H 0.7262 0.3067 0.5256 0.055 Uiso 1 1 calc R U
C16 C 0.09158(14) 0.34972(9) 0.61924(10) 0.0281(3) Uani 1 1 d . .
C17 C 0.03881(15) 0.38321(11) 0.55067(11) 0.0361(4) Uani 1 1 d . .
H17 H 0.0786 0.3807 0.5000 0.043 Uiso 1 1 calc R U
C18 C -0.07107(17) 0.42001(12) 0.55593(15) 0.0480(5) Uani 1 1 d . .
H18 H -0.1058 0.4430 0.5090 0.058 Uiso 1 1 calc R U
C19 C -0.13049(17) 0.42351(12) 0.62880(16) 0.0499(5) Uani 1 1 d . .
H19 H -0.2066 0.4480 0.6319 0.060 Uiso 1 1 calc R U
C20 C -0.07907(17) 0.39136(11) 0.69689(14) 0.0440(5) Uani 1 1 d . .
H20 H -0.1196 0.3943 0.7473 0.053 Uiso 1 1 calc R U
C21 C 0.03162(16) 0.35461(10) 0.69284(11) 0.0349(4) Uani 1 1 d . .
H21 H 0.0665 0.3328 0.7404 0.042 Uiso 1 1 calc R U
C22 C 0.05464(15) 0.17525(9) 0.68446(10) 0.0297(3) Uani 1 1 d . .
C23 C 0.05044(16) 0.18314(10) 0.76868(11) 0.0351(4) Uani 1 1 d . .
H23 H 0.1232 0.1920 0.7985 0.042 Uiso 1 1 calc R U
C24 C -0.05756(18) 0.17825(12) 0.80960(12) 0.0431(4) Uani 1 1 d . .
H24 H -0.0587 0.1844 0.8669 0.052 Uiso 1 1 calc R U
C25 C -0.16327(19) 0.16447(14) 0.76725(14) 0.0512(5) Uani 1 1 d . .
H25 H -0.2375 0.1612 0.7953 0.061 Uiso 1 1 calc R U
C26 C -0.16150(19) 0.15538(15) 0.68440(15) 0.0550(6) Uani 1 1 d . .
H26 H -0.2345 0.1454 0.6553 0.066 Uiso 1 1 calc R U
C27 C -0.05305(18) 0.16075(12) 0.64291(12) 0.0424(4) Uani 1 1 d . .
H27 H -0.0527 0.1544 0.5856 0.051 Uiso 1 1 calc R U
C28 C 0.34201(15) 0.15948(10) 0.68334(11) 0.0343(4) Uani 1 1 d . .
C29 C 0.40770(19) 0.09894(12) 0.65435(15) 0.0490(5) Uani 1 1 d . .
H29 H 0.3880 0.0779 0.6028 0.059 Uiso 1 1 calc R U
C30 C 0.5030(2) 0.06866(15) 0.7007(2) 0.0696(8) Uani 1 1 d . .
H30 H 0.5474 0.0271 0.6803 0.084 Uiso 1 1 calc R U
C31 C 0.5329(2) 0.09820(16) 0.7749(2) 0.0711(9) Uani 1 1 d . .
H31 H 0.5963 0.0765 0.8066 0.085 Uiso 1 1 calc R U
C32 C 0.4707(2) 0.15927(18) 0.80307(17) 0.0677(7) Uani 1 1 d . .
H32 H 0.4925 0.1808 0.8541 0.081 Uiso 1 1 calc R U
C33 C 0.37565(19) 0.19031(13) 0.75763(14) 0.0488(5) Uani 1 1 d . .
H33 H 0.3336 0.2329 0.7778 0.059 Uiso 1 1 calc R U
C34 C 0.18657(16) 0.14996(10) 0.51791(11) 0.0354(4) Uani 1 1 d . .
C35 C 0.1621(2) 0.07320(13) 0.51263(14) 0.0550(6) Uani 1 1 d . .
H35 H 0.1506 0.0447 0.5608 0.066 Uiso 1 1 calc R U
C36 C 0.1542(3) 0.03766(16) 0.43721(17) 0.0721(8) Uani 1 1 d . .
H36 H 0.1381 -0.0149 0.4343 0.087 Uiso 1 1 calc R U
C37 C 0.1695(3) 0.07808(18) 0.36768(15) 0.0693(8) Uani 1 1 d . .
H37 H 0.1645 0.0535 0.3165 0.083 Uiso 1 1 calc R U
C38 C 0.1921(2) 0.15394(16) 0.37136(13) 0.0593(6) Uani 1 1 d . .
H38 H 0.2016 0.1819 0.3227 0.071 Uiso 1 1 calc R U
C39 C 0.20118(19) 0.19035(12) 0.44624(11) 0.0422(4) Uani 1 1 d . .
H39 H 0.2174 0.2429 0.4484 0.051 Uiso 1 1 calc R U
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C34 Ge1 C28 111.01(8)
C34 Ge1 C22 108.62(7)
C28 Ge1 C22 110.30(7)
C34 Ge1 C1 108.96(7)
C28 Ge1 C1 111.62(7)
C22 Ge1 C1 106.18(7)
C3 O2 C4 109.40(13)
C3 N1 C2 119.64(13)
C3 N1 C5 112.57(13)
C2 N1 C5 124.10(13)
C2 C1 C16 121.59(14)
C2 C1 Ge1 119.93(12)
C16 C1 Ge1 118.08(11)
C1 C2 N1 121.48(14)
C1 C2 C8 123.33(15)
N1 C2 C8 115.09(13)
O1 C3 O2 122.36(15)
O1 C3 N1 127.81(16)
O2 C3 N1 109.83(14)
O2 C4 C5 106.94(14)
N1 C5 C7 111.61(14)
N1 C5 C6 111.69(15)
C7 C5 C6 111.05(17)
N1 C5 C4 99.04(13)
C7 C5 C4 111.47(17)
C6 C5 C4 111.47(15)
C9 C8 C2 173.38(18)
C8 C9 C10 177.9(2)
C11 C10 C15 119.38(18)
C11 C10 C9 120.26(18)
C15 C10 C9 120.34(18)
C10 C11 C12 119.4(2)
C13 C12 C11 121.2(3)
C12 C13 C14 119.7(2)
C13 C14 C15 120.6(2)
C14 C15 C10 119.7(2)
C21 C16 C17 118.56(16)
C21 C16 C1 122.04(15)
C17 C16 C1 119.33(15)
C18 C17 C16 120.49(18)
C19 C18 C17 120.5(2)
C20 C19 C18 119.64(18)
C19 C20 C21 120.66(19)
C20 C21 C16 120.18(18)
C27 C22 C23 117.82(16)
C27 C22 Ge1 119.90(13)
C23 C22 Ge1 121.78(13)
C24 C23 C22 121.31(17)
C25 C24 C23 119.94(19)
C26 C25 C24 119.97(19)
C25 C26 C27 120.27(19)
C22 C27 C26 120.68(19)
C29 C28 C33 118.31(19)
C29 C28 Ge1 120.90(16)
C33 C28 Ge1 120.70(15)
C28 C29 C30 120.3(2)
C31 C30 C29 120.7(3)
C30 C31 C32 119.4(2)
C31 C32 C33 120.6(3)
C28 C33 C32 120.6(2)
C35 C34 C39 118.39(18)
C35 C34 Ge1 119.18(15)
C39 C34 Ge1 122.42(14)
C34 C35 C36 120.5(2)
C37 C36 C35 120.3(2)
C36 C37 C38 120.2(2)
C37 C38 C39 120.3(2)
C34 C39 C38 120.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ge1 C34 1.9426(17)
Ge1 C28 1.9453(17)
Ge1 C22 1.9461(16)
Ge1 C1 1.9642(16)
O1 C3 1.204(2)
O2 C3 1.352(2)
O2 C4 1.437(2)
N1 C3 1.354(2)
N1 C2 1.434(2)
N1 C5 1.476(2)
C1 C2 1.349(2)
C1 C16 1.485(2)
C2 C8 1.434(2)
C4 C5 1.535(3)
C5 C7 1.521(3)
C5 C6 1.522(3)
C8 C9 1.196(2)
C9 C10 1.432(2)
C10 C11 1.389(3)
C10 C15 1.392(3)
C11 C12 1.394(3)
C12 C13 1.358(4)
C13 C14 1.374(4)
C14 C15 1.390(3)
C16 C21 1.393(2)
C16 C17 1.396(2)
C17 C18 1.384(3)
C18 C19 1.378(3)
C19 C20 1.374(3)
C20 C21 1.390(3)
C22 C27 1.389(2)
C22 C23 1.395(2)
C23 C24 1.384(3)
C24 C25 1.375(3)
C25 C26 1.374(3)
C26 C27 1.393(3)
C28 C29 1.385(3)
C28 C33 1.386(3)
C29 C30 1.400(3)
C30 C31 1.365(4)
C31 C32 1.368(4)
C32 C33 1.395(3)
C34 C35 1.390(3)
C34 C39 1.392(3)
C35 C36 1.394(3)
C36 C37 1.363(4)
C37 C38 1.369(4)
C38 C39 1.394(3)
