#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/17/4121729.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_4121729
loop_
_publ_author_name
'Li, Bijie'
'Driess, Matthias'
'Hartwig, John F.'
_publ_section_title
;
 Iridium-catalyzed regioselective silylation of secondary alkyl C-h bonds
 for the synthesis of 1,3-diols.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6586
_journal_page_last               6589
_journal_paper_doi               10.1021/ja5026479
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C18 H23 N O5'
_chemical_formula_weight         333.37
_chemical_name_common            BJL-1
_chemical_name_systematic
; 
 compound-5v 
;
_space_group.centring_type       C
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.539(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.6681(8)
_cell_length_b                   6.9135(2)
_cell_length_c                   18.1388(5)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.82
_cell_measurement_theta_min      3.32
_cell_volume                     3340.97(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2013
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_refln_scan_rate          20
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21428
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0446
_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)+(0.0532P)²+3.9875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2496
_reflns_number_total             3046
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5026479_si_001.cif
_cod_data_source_block           compound-5v
_cod_depositor_comments
;Adding full bibliography for 4121728--4121730.cif.

The following automatic conversions were performed:

'_space_group.centring_type' value 'C-centered' was replaced with the
value 'C' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4121729
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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'
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
C1 C 0.19368(7) 0.8798(2) 0.54402(9) 0.0216(4) Uani 1 1 d . .
C2 C 0.16908(7) 0.7058(3) 0.55394(10) 0.0231(4) Uani 1 1 d . .
H2 H 0.1365 0.6843 0.5323 0.028 Uiso 1 1 calc R U
C3 C 0.19326(6) 0.5640(2) 0.59611(10) 0.0221(4) Uani 1 1 d . .
H3 H 0.1772 0.4435 0.6037 0.027 Uiso 1 1 calc R U
C4 C 0.24112(6) 0.5980(2) 0.62736(9) 0.0202(4) Uani 1 1 d . .
C5 C 0.26491(6) 0.7746(2) 0.61596(9) 0.0216(4) Uani 1 1 d . .
H5 H 0.2976 0.7968 0.6371 0.026 Uiso 1 1 calc R U
C6 C 0.24107(7) 0.9174(2) 0.57409(10) 0.0223(4) Uani 1 1 d . .
H6 H 0.2569 1.0382 0.5663 0.027 Uiso 1 1 calc R U
C7 C 0.26532(6) 0.4436(2) 0.67425(10) 0.0212(4) Uani 1 1 d . .
C8 C 0.33998(7) 0.3312(2) 0.73624(10) 0.0229(4) Uani 1 1 d . .
H8 H 0.3196 0.2941 0.7790 0.027 Uiso 1 1 calc R U
C9 C 0.35283(7) 0.1542(3) 0.69011(11) 0.0316(5) Uani 1 1 d . .
H9A H 0.3300 0.1460 0.6457 0.038 Uiso 1 1 calc R U
H9B H 0.3493 0.0345 0.7193 0.038 Uiso 1 1 calc R U
C10 C 0.40730(8) 0.1786(3) 0.66783(12) 0.0355(5) Uani 1 1 d . .
H10A H 0.4287 0.0748 0.6898 0.043 Uiso 1 1 calc R U
H10B H 0.4093 0.1740 0.6135 0.043 Uiso 1 1 calc R U
C11 C 0.42409(7) 0.3762(3) 0.69746(11) 0.0293(4) Uani 1 1 d . .
H11A H 0.4193 0.4769 0.6590 0.035 Uiso 1 1 calc R U
H11B H 0.4599 0.3734 0.7143 0.035 Uiso 1 1 calc R U
C12 C 0.39061(6) 0.4151(2) 0.76211(10) 0.0228(4) Uani 1 1 d . .
H12 H 0.4036 0.3343 0.8045 0.027 Uiso 1 1 calc R U
C13 C 0.38957(6) 0.6248(2) 0.78880(10) 0.0220(4) Uani 1 1 d . .
H13 H 0.3800 0.7103 0.7460 0.026 Uiso 1 1 calc R U
C14 C 0.44016(7) 0.6910(3) 0.82227(11) 0.0271(4) Uani 1 1 d . .
H14 H 0.4658 0.6778 0.7840 0.033 Uiso 1 1 calc R U
C15 C 0.45795(7) 0.5737(3) 0.89108(11) 0.0297(4) Uani 1 1 d . .
H15A H 0.4293 0.5073 0.9130 0.036 Uiso 1 1 calc R U
H15B H 0.4831 0.4757 0.8780 0.036 Uiso 1 1 calc R U
C16 C 0.48112(10) 0.7214(3) 0.94489(14) 0.0493(6) Uani 1 1 d . .
H16A H 0.4803 0.6748 0.9964 0.059 Uiso 1 1 calc R U
H16B H 0.5162 0.7510 0.9332 0.059 Uiso 1 1 calc R U
C17 C 0.44735(10) 0.8966(3) 0.93243(14) 0.0503(7) Uani 1 1 d . .
H17A H 0.4638 1.0158 0.9517 0.060 Uiso 1 1 calc R U
H17B H 0.4151 0.8794 0.9565 0.060 Uiso 1 1 calc R U
C18 C 0.43947(8) 0.9048(3) 0.84849(12) 0.0355(5) Uani 1 1 d . .
H18A H 0.4667 0.9793 0.8263 0.043 Uiso 1 1 calc R U
H18B H 0.4069 0.9663 0.8344 0.043 Uiso 1 1 calc R U
N1 N 0.16815(6) 1.0299(2) 0.49865(8) 0.0248(3) Uani 1 1 d . .
O1 O 0.19033(5) 1.18294(18) 0.48908(8) 0.0315(3) Uani 1 1 d . .
O2 O 0.12592(5) 0.9946(2) 0.47231(8) 0.0341(3) Uani 1 1 d . .
O3 O 0.24318(5) 0.30259(17) 0.69636(7) 0.0268(3) Uani 1 1 d . .
O4 O 0.31388(4) 0.47772(16) 0.68969(7) 0.0215(3) Uani 1 1 d . .
O5 O 0.35340(4) 0.64737(18) 0.84398(7) 0.0251(3) Uani 1 1 d . .
H5A H 0.3253 0.6738 0.8237 0.038 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 122.89(16)
C6 C1 N1 118.77(15)
C2 C1 N1 118.34(16)
C3 C2 C1 118.34(16)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 120.07(16)
C2 C3 H3 120.0
C4 C3 H3 120.0
C3 C4 C5 120.10(16)
C3 C4 C7 118.44(15)
C5 C4 C7 121.44(15)
C6 C5 C4 120.31(16)
C6 C5 H5 119.8
C4 C5 H5 119.8
C1 C6 C5 118.28(16)
C1 C6 H6 120.9
C5 C6 H6 120.9
O3 C7 O4 123.59(16)
O3 C7 C4 123.80(16)
O4 C7 C4 112.60(14)
O4 C8 C12 107.69(13)
O4 C8 C9 110.36(14)
C12 C8 C9 104.85(14)
O4 C8 H8 111.2
C12 C8 H8 111.2
C9 C8 H8 111.2
C8 C9 C10 107.09(15)
C8 C9 H9A 110.3
C10 C9 H9A 110.3
C8 C9 H9B 110.3
C10 C9 H9B 110.3
H9A C9 H9B 108.6
C11 C10 C9 105.77(15)
C11 C10 H10A 110.6
C9 C10 H10A 110.6
C11 C10 H10B 110.6
C9 C10 H10B 110.6
H10A C10 H10B 108.7
C10 C11 C12 104.79(16)
C10 C11 H11A 110.8
C12 C11 H11A 110.8
C10 C11 H11B 110.8
C12 C11 H11B 110.8
H11A C11 H11B 108.9
C8 C12 C13 115.49(14)
C8 C12 C11 103.65(14)
C13 C12 C11 115.42(15)
C8 C12 H12 107.3
C13 C12 H12 107.3
C11 C12 H12 107.3
O5 C13 C14 107.52(14)
O5 C13 C12 110.35(14)
C14 C13 C12 112.50(14)
O5 C13 H13 108.8
C14 C13 H13 108.8
C12 C13 H13 108.8
C13 C14 C15 113.47(15)
C13 C14 C18 112.67(15)
C15 C14 C18 105.03(16)
C13 C14 H14 108.5
C15 C14 H14 108.5
C18 C14 H14 108.5
C16 C15 C14 105.49(16)
C16 C15 H15A 110.6
C14 C15 H15A 110.6
C16 C15 H15B 110.6
C14 C15 H15B 110.6
H15A C15 H15B 108.8
C17 C16 C15 102.58(17)
C17 C16 H16A 111.3
C15 C16 H16A 111.3
C17 C16 H16B 111.3
C15 C16 H16B 111.3
H16A C16 H16B 109.2
C16 C17 C18 103.40(19)
C16 C17 H17A 111.1
C18 C17 H17A 111.1
C16 C17 H17B 111.1
C18 C17 H17B 111.1
H17A C17 H17B 109.0
C17 C18 C14 105.49(16)
C17 C18 H18A 110.6
C14 C18 H18A 110.6
C17 C18 H18B 110.6
C14 C18 H18B 110.6
H18A C18 H18B 108.8
O2 N1 O1 123.73(15)
O2 N1 C1 118.07(15)
O1 N1 C1 118.20(15)
C7 O4 C8 115.36(13)
C13 O5 H5A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.379(2)
C1 C2 1.386(2)
C1 N1 1.472(2)
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.393(2)
C3 H3 0.9500
C4 C5 1.396(2)
C4 C7 1.494(2)
C5 C6 1.383(2)
C5 H5 0.9500
C6 H6 0.9500
C7 O3 1.217(2)
C7 O4 1.334(2)
C8 O4 1.474(2)
C8 C12 1.524(2)
C8 C9 1.529(3)
C8 H8 1.0000
C9 C10 1.534(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.527(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.529(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.529(2)
C12 H12 1.0000
C13 O5 1.429(2)
C13 C14 1.525(2)
C13 H13 1.0000
C14 C15 1.545(3)
C14 C18 1.553(3)
C14 H14 1.0000
C15 C16 1.524(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.520(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.529(3)
C17 H17A 0.9900
C17 H17B 0.9900
C18 H18A 0.9900
C18 H18B 0.9900
N1 O2 1.228(2)
N1 O1 1.2283(19)
O5 H5A 0.8400
