#------------------------------------------------------------------------------
#$Date: 2019-11-26 08:00:48 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243005 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/31/4133169.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_4133169
loop_
_publ_author_name
'Werner, Daniel'
'Anwander, Reiner'
_publ_section_title
;
 Unveiling the Takai Olefination Reagent via Tris( tert-butoxy)siloxy
 Variants.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14334
_journal_page_last               14341
_journal_paper_doi               10.1021/jacs.8b08739
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'I, 2(C6 H16 Cl Cr0.5 N2), C4 H8 O'
_chemical_formula_sum            'C16 H40 Cl2 Cr I N4 O'
_chemical_formula_weight         554.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.867(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.379(2)
_cell_length_b                   11.659(2)
_cell_length_c                   18.521(4)
_cell_measurement_reflns_used    2497
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.114
_cell_measurement_theta_min      2.256
_cell_volume                     2395.4(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1572
_diffrn_reflns_av_unetI/netI     0.1732
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20541
_diffrn_reflns_theta_full        26.15
_diffrn_reflns_theta_max         26.15
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1147 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.7728. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.357
_refine_diff_density_min         -1.768
_refine_diff_density_rms         0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1768
_refine_ls_R_factor_gt           0.1002
_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/[σ²(Fo²)+(0.0512P)²+2.5386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                3009
_reflns_number_total             4769
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8b08739_si_009.cif
_cod_data_source_block           7
_cod_original_cell_volume        2395.5(8)
_cod_database_code               4133169
_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. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C12) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,
 H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 '-x, -y, -z'
4 'x, -y, 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_calc_flag
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.43029(5) 0.26605(5) 0.56305(3) 0.01182(19) Uani 1 d 1 . . .
Cr1 Cr 1.0000 0.26303(16) 0.7500 0.0096(5) Uani 1 d 2 S T P
Cl1 Cl 1.0000 0.0657(2) 0.7500 0.0177(8) Uani 1 d 2 S T P
Cl2 Cl 1.0000 0.4604(2) 0.7500 0.0160(8) Uani 1 d 2 S T P
N1 N 1.1233(6) 0.2621(6) 0.6731(4) 0.0123(16) Uani 1 d 1 . . .
N2 N 0.8315(6) 0.2653(6) 0.6630(4) 0.0127(16) Uani 1 d 1 . U .
C1 C 1.1356(9) 0.3709(8) 0.6332(6) 0.029(3) Uani 1 d 1 . . .
H1A H 1.0573 0.3920 0.6018 0.043 Uiso 1 calc 1 GR . .
H1B H 1.1943 0.3603 0.6022 0.043 Uiso 1 calc 1 GR . .
H1C H 1.1633 0.4321 0.6692 0.043 Uiso 1 calc 1 GR . .
C2 C 1.1019(9) 0.1699(8) 0.6150(6) 0.032(3) Uani 1 d 1 . . .
H2A H 1.0896 0.0963 0.6378 0.048 Uiso 1 calc 1 GR . .
H2B H 1.1720 0.1643 0.5926 0.048 Uiso 1 calc 1 GR . .
H2C H 1.0302 0.1888 0.5766 0.048 Uiso 1 calc 1 GR . .
C3 C 0.7590(8) 0.2369(8) 0.7760(5) 0.023(2) Uani 1 d 1 . . .
H3A H 0.7537 0.1534 0.7659 0.028 Uiso 1 calc 1 R . .
H3B H 0.6934 0.2574 0.8008 0.028 Uiso 1 calc 1 R . .
C4 C 0.7407(9) 0.2978(10) 0.7061(6) 0.035(3) Uani 1 d 1 . . .
H4A H 0.7457 0.3814 0.7159 0.042 Uiso 1 calc 1 R . .
H4B H 0.6589 0.2809 0.6764 0.042 Uiso 1 calc 1 R . .
C5 C 0.7945(9) 0.1581(8) 0.6223(6) 0.033(3) Uani 1 d 1 . . .
H5A H 0.8547 0.1368 0.5942 0.049 Uiso 1 calc 1 GR . .
H5B H 0.7162 0.1693 0.5881 0.049 Uiso 1 calc 1 GR . .
H5C H 0.7879 0.0969 0.6574 0.049 Uiso 1 calc 1 GR . .
C6 C 0.8205(9) 0.3535(8) 0.6035(6) 0.032(3) Uani 1 d 1 . . .
H6A H 0.8466 0.4281 0.6258 0.049 Uiso 1 calc 1 GR . .
H6B H 0.7364 0.3585 0.5762 0.049 Uiso 1 calc 1 GR . .
H6C H 0.8715 0.3318 0.5695 0.049 Uiso 1 calc 1 GR . .
Cr2 Cr 0.5000 0.23423(16) 0.2500 0.0094(4) Uani 1 d 2 S T P
Cl3 Cl 0.70453(18) 0.23392(18) 0.25809(12) 0.0163(5) Uani 1 d 1 . . .
N3 N 0.5197(6) 0.0921(6) 0.3319(4) 0.0129(18) Uani 1 d 1 . . .
N4 N 0.5221(6) 0.3755(6) 0.3324(4) 0.0126(19) Uani 1 d 1 . . .
C7 C 0.6444(8) 0.0649(8) 0.3748(6) 0.025(3) Uani 1 d 1 . U .
H7A H 0.6969 0.0509 0.3403 0.037 Uiso 1 calc 1 GR . .
H7B H 0.6422 -0.0036 0.4050 0.037 Uiso 1 calc 1 GR . .
H7C H 0.6758 0.1298 0.4070 0.037 Uiso 1 calc 1 GR . .
C8 C 0.4446(9) 0.0991(7) 0.3867(6) 0.022(3) Uani 1 d 1 . . .
H8A H 0.4771 0.1579 0.4235 0.032 Uiso 1 calc 1 GR . .
H8B H 0.4448 0.0247 0.4114 0.032 Uiso 1 calc 1 GR . .
H8C H 0.3619 0.1192 0.3618 0.032 Uiso 1 calc 1 GR . .
C9 C 0.4767(9) -0.0093(7) 0.2842(6) 0.023(2) Uani 1 d 1 . U .
H9A H 0.5030 -0.0803 0.3125 0.027 Uiso 1 calc 1 R . .
H9B H 0.3875 -0.0091 0.2709 0.027 Uiso 1 calc 1 R . .
C10 C 0.4167(8) 0.4028(7) 0.3649(5) 0.016(2) Uani 1 d 1 . U .
H10A H 0.3469 0.4213 0.3251 0.024 Uiso 1 calc 1 GR . .
H10B H 0.4361 0.4687 0.3983 0.024 Uiso 1 calc 1 GR . .
H10C H 0.3978 0.3364 0.3927 0.024 Uiso 1 calc 1 GR . .
C11 C 0.6267(8) 0.3678(8) 0.3968(5) 0.020(2) Uani 1 d 1 . U .
H11A H 0.6089 0.3124 0.4327 0.031 Uiso 1 calc 1 GR . .
H11B H 0.6420 0.4433 0.4203 0.031 Uiso 1 calc 1 GR . .
H11C H 0.6982 0.3427 0.3798 0.031 Uiso 1 calc 1 GR . .
C12 C 0.5438(8) 0.4756(7) 0.2862(5) 0.016(2) Uani 1 d 1 . U .
H12A H 0.5360 0.5479 0.3128 0.019 Uiso 1 calc 1 R . .
H12B H 0.6267 0.4716 0.2781 0.019 Uiso 1 calc 1 R . .
O1 O -0.0627(5) 0.2441(5) 0.4455(3) 0.0236(16) Uani 1 d 1 . . .
C13 C -0.0245(9) 0.1422(8) 0.4133(6) 0.027(3) Uani 1 d 1 . . .
H13A H -0.0802 0.1242 0.3655 0.032 Uiso 1 calc 1 R . .
H13B H -0.0215 0.0758 0.4470 0.032 Uiso 1 calc 1 R . .
C14 C 0.1008(9) 0.1707(9) 0.4020(6) 0.032(3) Uani 1 d 1 . . .
H14A H 0.1638 0.1435 0.4443 0.038 Uiso 1 calc 1 R . .
H14B H 0.1143 0.1351 0.3560 0.038 Uiso 1 calc 1 R . .
C15 C 0.1022(10) 0.2996(9) 0.3967(7) 0.044(4) Uani 1 d 1 . . .
H15A H 0.1108 0.3242 0.3470 0.053 Uiso 1 calc 1 R . .
H15B H 0.1694 0.3322 0.4344 0.053 Uiso 1 calc 1 R . .
C16 C -0.0184(9) 0.3373(8) 0.4106(6) 0.028(3) Uani 1 d 1 . . .
H16A H -0.0083 0.4059 0.4429 0.033 Uiso 1 calc 1 R . .
H16B H -0.0750 0.3562 0.3633 0.033 Uiso 1 calc 1 R . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
Cl2 Cr1 Cl1 180.000(1) . .
N1 Cr1 Cl1 89.72(18) 2_756 .
N1 Cr1 Cl1 89.72(18) . .
N1 Cr1 Cl2 90.28(18) . .
N1 Cr1 Cl2 90.28(18) 2_756 .
N1 Cr1 N1 179.4(4) . 2_756
N1 Cr1 N2 95.8(2) 2_756 2_756
N1 Cr1 N2 84.2(3) . 2_756
N1 Cr1 N2 95.9(2) . .
N1 Cr1 N2 84.2(3) 2_756 .
N2 Cr1 Cl1 90.69(18) . .
N2 Cr1 Cl1 90.69(18) 2_756 .
N2 Cr1 Cl2 89.31(18) 2_756 .
N2 Cr1 Cl2 89.31(18) . .
N2 Cr1 N2 178.6(4) . 2_756
C1 N1 Cr1 117.3(5) . .
C1 N1 C2 105.8(7) . .
C2 N1 Cr1 116.1(5) . .
C3 N1 Cr1 101.7(5) 2_756 .
C3 N1 C1 108.2(7) 2_756 .
C3 N1 C2 107.0(7) 2_756 .
C4 N2 Cr1 101.8(6) . .
C4 N2 C6 105.5(7) . .
C5 N2 Cr1 117.7(6) . .
C5 N2 C4 109.7(7) . .
C5 N2 C6 103.9(7) . .
C6 N2 Cr1 117.5(6) . .
C4 C3 N1 113.6(8) . 2_756
C3 C4 N2 112.0(8) . .
Cl3 Cr2 Cl3 179.82(14) 2_655 .
N3 Cr2 Cl3 90.44(19) 2_655 2_655
N3 Cr2 Cl3 89.42(19) . 2_655
N3 Cr2 Cl3 90.45(19) . .
N3 Cr2 Cl3 89.42(19) 2_655 .
N3 Cr2 N3 83.7(4) . 2_655
N4 Cr2 Cl3 90.22(19) 2_655 .
N4 Cr2 Cl3 90.23(19) . 2_655
N4 Cr2 Cl3 89.91(19) . .
N4 Cr2 Cl3 89.91(19) 2_655 2_655
N4 Cr2 N3 96.0(2) 2_655 2_655
N4 Cr2 N3 179.3(3) . 2_655
N4 Cr2 N3 96.0(2) . .
N4 Cr2 N3 179.3(3) 2_655 .
N4 Cr2 N4 84.3(4) . 2_655
C7 N3 Cr2 117.3(5) . .
C8 N3 Cr2 116.4(5) . .
C8 N3 C7 105.9(8) . .
C8 N3 C9 106.8(7) . .
C9 N3 Cr2 102.5(6) . .
C9 N3 C7 107.1(7) . .
C10 N4 Cr2 117.2(5) . .
C10 N4 C12 108.3(7) . .
C11 N4 Cr2 117.0(5) . .
C11 N4 C10 105.2(7) . .
C11 N4 C12 107.5(7) . .
C12 N4 Cr2 101.1(5) . .
C9 C9 N3 112.0(6) 2_655 .
C12 C12 N4 110.7(6) 2_655 .
C16 O1 C13 105.8(7) . .
O1 C13 C14 104.8(8) . .
C15 C14 C13 104.5(8) . .
C14 C15 C16 104.8(8) . .
O1 C16 C15 106.5(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cr1 Cl1 2.301(3) .
Cr1 Cl2 2.301(3) .
Cr1 N1 2.211(7) .
Cr1 N1 2.211(7) 2_756
Cr1 N2 2.213(7) .
Cr1 N2 2.213(7) 2_756
N1 C1 1.491(10) .
N1 C2 1.502(11) .
N1 C3 1.487(11) 2_756
N2 C4 1.489(11) .
N2 C5 1.472(11) .
N2 C6 1.492(12) .
C3 N1 1.487(11) 2_756
C3 C4 1.450(13) .
Cr2 Cl3 2.299(2) .
Cr2 Cl3 2.299(2) 2_655
Cr2 N3 2.224(7) 2_655
Cr2 N3 2.224(7) .
Cr2 N4 2.222(7) 2_655
Cr2 N4 2.222(7) .
N3 C7 1.498(11) .
N3 C8 1.467(11) .
N3 C9 1.491(11) .
N4 C10 1.491(10) .
N4 C11 1.488(11) .
N4 C12 1.500(11) .
C9 C9 1.480(18) 2_655
C12 C12 1.482(17) 2_655
O1 C13 1.440(11) .
O1 C16 1.414(10) .
C13 C14 1.524(13) .
C14 C15 1.506(14) .
C15 C16 1.517(13) .
