#------------------------------------------------------------------------------
#$Date: 2015-07-04 14:08:53 +0300 (Sat, 04 Jul 2015) $
#$Revision: 140009 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/38/4123893.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_4123893
loop_
_publ_author_name
'Dao, Hai T.'
'Li, Chao'
'Michaudel, Quentin'
'Maxwell, Brad D.'
'Baran, Phil S.'
_publ_section_title
;
 Hydromethylation of Unactivated Olefins.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8046
_journal_page_last               8049
_journal_paper_doi               10.1021/jacs.5b05144
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 O6'
_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_weight         308.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-20
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0153(3)
_cell_length_b                   11.9330(5)
_cell_length_c                   17.6064(8)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.409
_cell_measurement_theta_min      4.476
_cell_volume                     1473.89(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23366
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.403
_diffrn_reflns_theta_min         4.476
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.3135
_exptl_absorpt_correction_T_min  0.2144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1125 before and 0.0836 after correction.
The Ratio of minimum to maximum transmission is 0.6839.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1152 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0281
_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)+(0.0388P)²+0.3249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.709
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     0.990
_reflns_number_gt                2794
_reflns_number_total             2805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b05144_si_003.cif
_cod_data_source_block           Baran498
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/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 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               4123893
_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_max   0.906
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-H4
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.36511(17) 0.83937(11) 0.68586(7) 0.0197(3) Uani 1 1 d .
O2 O 0.40515(17) 0.66231(10) 0.72334(7) 0.0186(3) Uani 1 1 d .
O3 O 0.55946(18) 0.48852(10) 0.65047(7) 0.0207(3) Uani 1 1 d .
O4 O 0.98738(18) 0.78694(11) 0.72072(7) 0.0216(3) Uani 1 1 d D
H4 H 1.083(4) 0.792(3) 0.6883(15) 0.050(8) Uiso 1 1 d D
O5 O 0.73496(19) 0.68702(11) 0.51719(7) 0.0217(3) Uani 1 1 d .
O6 O 0.40732(19) 0.52604(11) 0.54091(7) 0.0252(3) Uani 1 1 d .
C1 C 0.4646(2) 0.76983(14) 0.71613(9) 0.0158(3) Uani 1 1 d .
C2 C 0.6631(2) 0.78109(15) 0.74923(9) 0.0166(3) Uani 1 1 d .
H2 H 0.6815 0.8571 0.7720 0.020 Uiso 1 1 calc R
C3 C 0.6459(3) 0.69070(14) 0.81221(9) 0.0185(4) Uani 1 1 d .
H3 H 0.5384 0.7184 0.8445 0.022 Uiso 1 1 calc R
C4 C 0.5540(3) 0.59916(14) 0.76364(9) 0.0182(4) Uani 1 1 d .
H4A H 0.4969 0.5392 0.7962 0.022 Uiso 1 1 calc R
C5 C 0.6848(2) 0.54893(14) 0.70329(9) 0.0173(4) Uani 1 1 d .
H5 H 0.7758 0.4953 0.7275 0.021 Uiso 1 1 calc R
C6 C 0.7964(2) 0.63504(14) 0.65424(9) 0.0169(4) Uani 1 1 d .
C7 C 0.8117(2) 0.75947(15) 0.68615(10) 0.0173(4) Uani 1 1 d .
C8 C 0.7690(3) 0.83366(15) 0.61557(10) 0.0192(4) Uani 1 1 d .
H8A H 0.7079 0.9048 0.6311 0.023 Uiso 1 1 calc R
H8B H 0.8881 0.8511 0.5879 0.023 Uiso 1 1 calc R
C9 C 0.6355(3) 0.76566(15) 0.56604(10) 0.0195(4) Uani 1 1 d .
H9 H 0.5069 0.7952 0.5518 0.023 Uiso 1 1 calc R
C10 C 0.6612(2) 0.64722(15) 0.58780(9) 0.0176(4) Uani 1 1 d .
C11 C 0.5237(3) 0.55143(14) 0.58736(9) 0.0186(4) Uani 1 1 d .
C12 C 0.8029(3) 0.66037(16) 0.87078(10) 0.0248(4) Uani 1 1 d .
C13 C 0.9755(3) 0.59401(17) 0.84203(11) 0.0276(4) Uani 1 1 d .
H13A H 0.9337 0.5201 0.8244 0.041 Uiso 1 1 calc GR
H13B H 1.0677 0.5849 0.8834 0.041 Uiso 1 1 calc GR
H13C H 1.0354 0.6346 0.7999 0.041 Uiso 1 1 calc GR
C14 C 0.7039(4) 0.5890(2) 0.93267(11) 0.0351(5) Uani 1 1 d .
H14A H 0.5927 0.6295 0.9522 0.053 Uiso 1 1 calc GR
H14B H 0.7935 0.5747 0.9743 0.053 Uiso 1 1 calc GR
H14C H 0.6626 0.5175 0.9107 0.053 Uiso 1 1 calc GR
C15 C 0.8735(4) 0.77028(18) 0.90598(13) 0.0379(5) Uani 1 1 d .
H15A H 0.9460 0.8126 0.8680 0.057 Uiso 1 1 calc GR
H15B H 0.9557 0.7536 0.9496 0.057 Uiso 1 1 calc GR
H15C H 0.7641 0.8148 0.9228 0.057 Uiso 1 1 calc GR
C16 C 0.9896(3) 0.58803(16) 0.62963(11) 0.0226(4) Uani 1 1 d .
H16A H 0.9706 0.5168 0.6029 0.034 Uiso 1 1 calc GR
H16B H 1.0695 0.5756 0.6745 0.034 Uiso 1 1 calc GR
H16C H 1.0526 0.6415 0.5957 0.034 Uiso 1 1 calc GR
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'
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
C1 O2 C4 108.17(13)
C11 O3 C5 110.84(13)
C7 O4 H4 114(2)
C10 O5 C9 61.64(11)
O1 C1 O2 120.90(16)
O1 C1 C2 129.76(16)
O2 C1 C2 109.32(14)
C1 C2 H2 110.7
C1 C2 C3 98.15(13)
C1 C2 C7 109.20(13)
C3 C2 H2 110.7
C7 C2 H2 110.7
C7 C2 C3 116.75(14)
C2 C3 H3 103.6
C4 C3 C2 97.45(13)
C4 C3 H3 103.6
C4 C3 C12 120.28(15)
C12 C3 C2 125.59(16)
C12 C3 H3 103.6
O2 C4 C3 101.73(13)
O2 C4 H4A 111.0
O2 C4 C5 106.99(13)
C3 C4 H4A 111.0
C5 C4 C3 114.58(14)
C5 C4 H4A 111.0
O3 C5 C4 105.88(13)
O3 C5 H5 109.8
O3 C5 C6 105.92(13)
C4 C5 H5 109.8
C4 C5 C6 115.48(14)
C6 C5 H5 109.8
C5 C6 C7 117.04(14)
C10 C6 C5 100.21(14)
C10 C6 C7 103.04(13)
C10 C6 C16 111.82(14)
C16 C6 C5 111.20(14)
C16 C6 C7 112.50(14)
O4 C7 C2 103.90(14)
O4 C7 C6 115.30(14)
O4 C7 C8 112.35(14)
C2 C7 C6 111.36(14)
C2 C7 C8 110.45(14)
C8 C7 C6 103.65(13)
C7 C8 H8A 110.6
C7 C8 H8B 110.6
H8A C8 H8B 108.7
C9 C8 C7 105.92(14)
C9 C8 H8A 110.6
C9 C8 H8B 110.6
O5 C9 C8 112.95(15)
O5 C9 H9 120.9
O5 C9 C10 58.38(10)
C8 C9 H9 120.9
C10 C9 C8 106.72(14)
C10 C9 H9 120.9
O5 C10 C6 118.56(14)
O5 C10 C9 59.98(11)
O5 C10 C11 118.90(14)
C9 C10 C6 111.69(15)
C9 C10 C11 130.66(16)
C11 C10 C6 109.57(15)
O3 C11 C10 107.31(14)
O6 C11 O3 122.93(16)
O6 C11 C10 129.66(16)
C13 C12 C3 117.50(15)
C13 C12 C14 107.63(16)
C13 C12 C15 108.68(19)
C14 C12 C3 106.11(17)
C15 C12 C3 107.37(15)
C15 C12 C14 109.35(17)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C6 C16 H16A 109.5
C6 C16 H16B 109.5
C6 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.208(2)
O2 C1 1.355(2)
O2 C4 1.470(2)
O3 C5 1.469(2)
O3 C11 1.364(2)
O4 H4 0.89(2)
O4 C7 1.413(2)
O5 C9 1.452(2)
O5 C10 1.428(2)
O6 C11 1.195(2)
C1 C2 1.515(2)
C2 H2 1.0000
C2 C3 1.552(2)
C2 C7 1.545(2)
C3 H3 1.0000
C3 C4 1.530(2)
C3 C12 1.552(2)
C4 H4A 1.0000
C4 C5 1.527(2)
C5 H5 1.0000
C5 C6 1.554(2)
C6 C7 1.591(2)
C6 C10 1.513(2)
C6 C16 1.529(2)
C7 C8 1.555(2)
C8 H8A 0.9900
C8 H8B 0.9900
C8 C9 1.515(2)
C9 H9 1.0000
C9 C10 1.476(2)
C10 C11 1.496(2)
C12 C13 1.533(3)
C12 C14 1.548(3)
C12 C15 1.533(3)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
