#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:48:26 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253726 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/50/4135061.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_4135061
loop_
_publ_author_name
'Debrauwer, Vincent'
'Turlik, Aneta'
'Rummler, Lénaic'
'Prescimone, Alessandro'
'Blanchard, Nicolas'
'Houk, K. N.'
'Bizet, Vincent'
_publ_section_title
;
 Ligand-Controlled Regiodivergent Palladium-Catalyzed Hydrogermylation of
 Ynamides.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11153
_journal_page_last               11164
_journal_paper_doi               10.1021/jacs.0c03556
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C29 H25 Ge1 N1 O2'
_chemical_formula_sum            'C29 H25 Ge N O2'
_chemical_formula_weight         492.11
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                94.497(8)
_cell_angle_beta                 103.341(7)
_cell_angle_gamma                119.914(6)
_cell_formula_units_Z            2
_cell_length_a                   10.3008(8)
_cell_length_b                   10.3151(9)
_cell_length_c                   13.5595(14)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    123
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1182.7(2)
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie 2011)'
_computing_data_collection       'STOE X-AREA (Stoe & Cie 2011)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie 1996)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18560
_diffrn_reflns_theta_full        52.800
_diffrn_reflns_theta_max         54.313
_diffrn_reflns_theta_min         2.994
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_source_voltage           70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
; 
 
;
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.05
_refine_diff_density_min         -0.80
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0623
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.0005549
_refine_ls_shift/su_mean         0.0001505
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.733 0.662 0.248 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0640
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0583
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3531
_reflns_number_total             4221
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0474
_oxford_refine_ls_scale          0.5800(12)
_oxford_reflns_number_all        4203
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_cod_data_source_file            ja0c03556_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4135061--4135063.cif.
;
_cod_original_formula_sum        'C29 H25 Ge1 N1 O2'
_cod_database_code               4135061
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ge1 Ge 0.38032(4) 0.41782(3) 0.26138(3) 0.0416 1.0000 Uani . . . . . .
N1 N 0.1599(3) 0.4187(3) -0.04022(19) 0.0458 1.0000 Uani . . . . . .
O1 O 0.0104(3) 0.4495(3) -0.17091(18) 0.0600 1.0000 Uani . . . . . .
O2 O 0.1434(3) 0.6343(3) -0.02425(19) 0.0595 1.0000 Uani . . . . . .
C1 C 0.3001(3) 0.3678(3) 0.1090(2) 0.0416 1.0000 Uani . . . . . .
C2 C 0.2384(3) 0.4436(3) 0.0651(2) 0.0434 1.0000 Uani . . . . . .
C3 C 0.1087(4) 0.5126(4) -0.0728(3) 0.0514 1.0000 Uani . . . . . .
C4 C -0.0262(5) 0.2948(4) -0.2002(3) 0.0611 1.0000 Uani . . . . . .
C5 C 0.1052(4) 0.2897(4) -0.1249(2) 0.0536 1.0000 Uani . . . . . .
C6 C 0.2269(3) 0.2501(3) 0.3091(2) 0.0437 1.0000 Uani . . . . . .
C7 C 0.0660(4) 0.1903(4) 0.2644(3) 0.0520 1.0000 Uani . . . . . .
C8 C -0.0444(4) 0.0674(4) 0.2934(3) 0.0584 1.0000 Uani . . . . . .
C9 C 0.0037(4) 0.0028(4) 0.3672(3) 0.0562 1.0000 Uani . . . . . .
C10 C 0.1634(4) 0.0619(4) 0.4133(3) 0.0550 1.0000 Uani . . . . . .
C11 C 0.2742(4) 0.1853(3) 0.3836(2) 0.0486 1.0000 Uani . . . . . .
C12 C 0.4050(3) 0.6124(3) 0.3143(2) 0.0424 1.0000 Uani . . . . . .
C13 C 0.3256(4) 0.6240(4) 0.3820(2) 0.0487 1.0000 Uani . . . . . .
C14 C 0.3379(4) 0.7624(4) 0.4138(3) 0.0553 1.0000 Uani . . . . . .
C15 C 0.4263(4) 0.8888(4) 0.3772(3) 0.0554 1.0000 Uani . . . . . .
C16 C 0.5071(4) 0.8788(4) 0.3109(3) 0.0550 1.0000 Uani . . . . . .
C17 C 0.4972(4) 0.7425(3) 0.2808(2) 0.0500 1.0000 Uani . . . . . .
C18 C 0.5828(3) 0.4341(3) 0.3075(2) 0.0432 1.0000 Uani . . . . . .
C19 C 0.7114(4) 0.5643(3) 0.3804(2) 0.0481 1.0000 Uani . . . . . .
C20 C 0.8570(4) 0.5794(4) 0.4139(3) 0.0559 1.0000 Uani . . . . . .
C21 C 0.8765(4) 0.4641(4) 0.3744(3) 0.0548 1.0000 Uani . . . . . .
C22 C 0.7497(4) 0.3340(4) 0.3030(3) 0.0538 1.0000 Uani . . . . . .
C23 C 0.6038(4) 0.3178(4) 0.2701(3) 0.0506 1.0000 Uani . . . . . .
C24 C 0.3074(3) 0.2414(3) 0.0554(2) 0.0425 1.0000 Uani . . . . . .
C25 C 0.4229(4) 0.2726(4) 0.0079(2) 0.0511 1.0000 Uani . . . . . .
C26 C 0.4337(4) 0.1550(4) -0.0376(3) 0.0555 1.0000 Uani . . . . . .
C27 C 0.3281(4) 0.0035(4) -0.0376(3) 0.0536 1.0000 Uani . . . . . .
C28 C 0.2138(4) -0.0288(4) 0.0097(3) 0.0527 1.0000 Uani . . . . . .
C29 C 0.2048(3) 0.0887(3) 0.0570(2) 0.0473 1.0000 Uani . . . . . .
H21 H 0.2473 0.5243 0.1084 0.0522 1.0000 Uiso R . . . . .
H41 H -0.0300 0.2710 -0.2720 0.0728 1.0000 Uiso R . . . . .
H42 H -0.1257 0.2242 -0.1901 0.0730 1.0000 Uiso R . . . . .
H51 H 0.1882 0.3037 -0.1548 0.0640 1.0000 Uiso R . . . . .
H52 H 0.0651 0.1940 -0.1008 0.0636 1.0000 Uiso R . . . . .
H71 H 0.0335 0.2340 0.2149 0.0621 1.0000 Uiso R . . . . .
H81 H -0.1520 0.0276 0.2624 0.0694 1.0000 Uiso R . . . . .
H91 H -0.0694 -0.0797 0.3860 0.0665 1.0000 Uiso R . . . . .
H101 H 0.1953 0.0186 0.4640 0.0659 1.0000 Uiso R . . . . .
H111 H 0.3821 0.2250 0.4138 0.0578 1.0000 Uiso R . . . . .
H131 H 0.2634 0.5383 0.4064 0.0579 1.0000 Uiso R . . . . .
H141 H 0.2864 0.7707 0.4604 0.0660 1.0000 Uiso R . . . . .
H151 H 0.4321 0.9814 0.3964 0.0667 1.0000 Uiso R . . . . .
H161 H 0.5668 0.9646 0.2861 0.0659 1.0000 Uiso R . . . . .
H171 H 0.5519 0.7374 0.2353 0.0599 1.0000 Uiso R . . . . .
H191 H 0.6997 0.6430 0.4075 0.0584 1.0000 Uiso R . . . . .
H201 H 0.9412 0.6672 0.4629 0.0666 1.0000 Uiso R . . . . .
H211 H 0.9744 0.4744 0.3949 0.0656 1.0000 Uiso R . . . . .
H221 H 0.7634 0.2563 0.2759 0.0651 1.0000 Uiso R . . . . .
H231 H 0.5207 0.2286 0.2216 0.0606 1.0000 Uiso R . . . . .
H251 H 0.4916 0.3724 0.0060 0.0604 1.0000 Uiso R . . . . .
H261 H 0.5137 0.1788 -0.0679 0.0670 1.0000 Uiso R . . . . .
H271 H 0.3335 -0.0760 -0.0696 0.0640 1.0000 Uiso R . . . . .
H281 H 0.1417 -0.1314 0.0092 0.0632 1.0000 Uiso R . . . . .
H291 H 0.1290 0.0669 0.0914 0.0562 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0137 0.0067 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ge -1.5186 0.6907 16.0816 2.8509 6.3747 0.2516 3.7068 11.4468 3.6830 54.7625
2.1313 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0241 0.0134 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0389 0.0241 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . Ge1 . C6 . 107.33(12) yes
C1 . Ge1 . C12 . 108.72(12) yes
C6 . Ge1 . C12 . 111.37(12) yes
C1 . Ge1 . C18 . 110.41(12) yes
C6 . Ge1 . C18 . 109.24(12) yes
C12 . Ge1 . C18 . 109.74(12) yes
C2 . N1 . C3 . 120.5(3) yes
C2 . N1 . C5 . 128.0(2) yes
C3 . N1 . C5 . 111.1(3) yes
C3 . O1 . C4 . 108.8(2) yes
Ge1 . C1 . C2 . 117.4(2) yes
Ge1 . C1 . C24 . 115.45(19) yes
C2 . C1 . C24 . 127.0(3) yes
N1 . C2 . C1 . 128.3(3) yes
N1 . C2 . H21 . 114.1 no
C1 . C2 . H21 . 117.6 no
N1 . C3 . O1 . 109.8(3) yes
N1 . C3 . O2 . 127.4(3) yes
O1 . C3 . O2 . 122.8(3) yes
O1 . C4 . C5 . 105.2(3) yes
O1 . C4 . H41 . 110.8 no
C5 . C4 . H41 . 111.5 no
O1 . C4 . H42 . 108.9 no
C5 . C4 . H42 . 109.3 no
H41 . C4 . H42 . 111.0 no
C4 . C5 . N1 . 100.1(3) yes
C4 . C5 . H51 . 112.5 no
N1 . C5 . H51 . 112.4 no
C4 . C5 . H52 . 112.0 no
N1 . C5 . H52 . 110.5 no
H51 . C5 . H52 . 109.2 no
Ge1 . C6 . C7 . 119.7(2) yes
Ge1 . C6 . C11 . 121.2(2) yes
C7 . C6 . C11 . 119.1(3) yes
C6 . C7 . C8 . 120.6(3) yes
C6 . C7 . H71 . 119.5 no
C8 . C7 . H71 . 119.8 no
C7 . C8 . C9 . 119.9(3) yes
C7 . C8 . H81 . 119.9 no
C9 . C8 . H81 . 120.2 no
C8 . C9 . C10 . 120.2(3) yes
C8 . C9 . H91 . 120.2 no
C10 . C9 . H91 . 119.7 no
C9 . C10 . C11 . 119.7(3) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 120.5 no
C10 . C11 . C6 . 120.4(3) yes
C10 . C11 . H111 . 120.2 no
C6 . C11 . H111 . 119.4 no
Ge1 . C12 . C13 . 121.6(2) yes
Ge1 . C12 . C17 . 120.0(2) yes
C13 . C12 . C17 . 118.3(3) yes
C12 . C13 . C14 . 120.5(3) yes
C12 . C13 . H131 . 120.1 no
C14 . C13 . H131 . 119.4 no
C13 . C14 . C15 . 120.3(3) yes
C13 . C14 . H141 . 120.3 no
C15 . C14 . H141 . 119.4 no
C14 . C15 . C16 . 119.6(3) yes
C14 . C15 . H151 . 120.7 no
C16 . C15 . H151 . 119.7 no
C15 . C16 . C17 . 120.1(3) yes
C15 . C16 . H161 . 119.5 no
C17 . C16 . H161 . 120.4 no
C12 . C17 . C16 . 121.1(3) yes
C12 . C17 . H171 . 119.8 no
C16 . C17 . H171 . 119.0 no
Ge1 . C18 . C19 . 119.8(2) yes
Ge1 . C18 . C23 . 121.8(2) yes
C19 . C18 . C23 . 118.3(3) yes
C18 . C19 . C20 . 121.0(3) yes
C18 . C19 . H191 . 119.9 no
C20 . C19 . H191 . 119.1 no
C19 . C20 . C21 . 119.9(3) yes
C19 . C20 . H201 . 119.6 no
C21 . C20 . H201 . 120.5 no
C20 . C21 . C22 . 119.6(3) yes
C20 . C21 . H211 . 120.6 no
C22 . C21 . H211 . 119.7 no
C21 . C22 . C23 . 120.7(3) yes
C21 . C22 . H221 . 119.5 no
C23 . C22 . H221 . 119.8 no
C18 . C23 . C22 . 120.4(3) yes
C18 . C23 . H231 . 121.0 no
C22 . C23 . H231 . 118.5 no
C1 . C24 . C25 . 120.9(3) yes
C1 . C24 . C29 . 120.8(3) yes
C25 . C24 . C29 . 118.1(3) yes
C24 . C25 . C26 . 120.6(3) yes
C24 . C25 . H251 . 119.4 no
C26 . C25 . H251 . 119.9 no
C25 . C26 . C27 . 120.4(3) yes
C25 . C26 . H261 . 119.2 no
C27 . C26 . H261 . 120.4 no
C26 . C27 . C28 . 119.5(3) yes
C26 . C27 . H271 . 120.6 no
C28 . C27 . H271 . 119.9 no
C27 . C28 . C29 . 120.2(3) yes
C27 . C28 . H281 . 119.6 no
C29 . C28 . H281 . 120.2 no
C24 . C29 . C28 . 121.0(3) yes
C24 . C29 . H291 . 118.8 no
C28 . C29 . H291 . 120.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ge1 . C1 . 1.959(3) yes
Ge1 . C6 . 1.957(3) yes
Ge1 . C12 . 1.947(3) yes
Ge1 . C18 . 1.950(3) yes
N1 . C2 . 1.401(4) yes
N1 . C3 . 1.372(4) yes
N1 . C5 . 1.456(4) yes
O1 . C3 . 1.343(4) yes
O1 . C4 . 1.442(4) yes
O2 . C3 . 1.204(4) yes
C1 . C2 . 1.327(4) yes
C1 . C24 . 1.486(4) yes
C2 . H21 . 0.932 no
C4 . C5 . 1.523(5) yes
C4 . H41 . 0.971 no
C4 . H42 . 0.968 no
C5 . H51 . 0.981 no
C5 . H52 . 0.979 no
C6 . C7 . 1.397(4) yes
C6 . C11 . 1.382(4) yes
C7 . C8 . 1.379(4) yes
C7 . H71 . 0.927 no
C8 . C9 . 1.378(5) yes
C8 . H81 . 0.937 no
C9 . C10 . 1.390(5) yes
C9 . H91 . 0.916 no
C10 . C11 . 1.388(5) yes
C10 . H101 . 0.934 no
C11 . H111 . 0.939 no
C12 . C13 . 1.397(4) yes
C12 . C17 . 1.391(4) yes
C13 . C14 . 1.392(5) yes
C13 . H131 . 0.939 no
C14 . C15 . 1.379(5) yes
C14 . H141 . 0.938 no
C15 . C16 . 1.388(5) yes
C15 . H151 . 0.939 no
C16 . C17 . 1.379(4) yes
C16 . H161 . 0.934 no
C17 . H171 . 0.941 no
C18 . C19 . 1.395(4) yes
C18 . C23 . 1.400(4) yes
C19 . C20 . 1.386(5) yes
C19 . H191 . 0.938 no
C20 . C21 . 1.389(5) yes
C20 . H201 . 0.933 no
C21 . C22 . 1.381(5) yes
C21 . H211 . 0.930 no
C22 . C23 . 1.384(4) yes
C22 . H221 . 0.942 no
C23 . H231 . 0.933 no
C24 . C25 . 1.392(4) yes
C24 . C29 . 1.398(4) yes
C25 . C26 . 1.384(5) yes
C25 . H251 . 0.920 no
C26 . C27 . 1.389(5) yes
C26 . H261 . 0.937 no
C27 . C28 . 1.378(5) yes
C27 . H271 . 0.930 no
C28 . C29 . 1.382(4) yes
C28 . H281 . 0.941 no
C29 . H291 . 0.940 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C28 . H281 . O2 1_545 132 0.94 2.43 3.145(5) yes
