#------------------------------------------------------------------------------
#$Date: 2018-01-31 02:15:08 +0200 (Wed, 31 Jan 2018) $
#$Revision: 205915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127102.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_4127102
loop_
_publ_author_name
'Tindall, Daniel J.'
'Werlé, Christophe'
'Goddard, Richard'
'Philipps, Petra'
'Farès, Christophe'
'Fürstner, Alois'
_publ_section_title
;
 Structure and Reactivity of Half-Sandwich Rh(+3) and Ir(+3) Carbene
 Complexes. Catalytic Metathesis of Azobenzene Derivatives.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12673
_journal_year                    2018
_chemical_compound_source        'hexane, ethylacetate'
_chemical_formula_moiety         'C18 H18 O5'
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_chemical_name_systematic
;
 methyl (2SR,3SR)-2-(4-methoxyphenyl)-3-(4-methoxyphenyl)oxirane-
 2-carboxylate
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                TID-TA-302-05_10010_200_K
_audit_creation_date             2016-05-02
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 105.473(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.6824(14)
_cell_length_b                   7.8512(14)
_cell_length_c                   11.2312(16)
_cell_measurement_reflns_used    57166
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      33.0995
_cell_measurement_theta_min      2.6481
_cell_volume                     3202.3(8)
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            52194
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.186
_diffrn_reflns_theta_min         2.654
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.99333
_exptl_absorpt_correction_T_min  0.98531
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         6110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0878
_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)+(0.0806P)²+12.5834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2735
_refine_ls_wR_factor_ref         0.2854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4523
_reflns_number_total             6110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12673_si_002.cif
_cod_data_source_block           8
_cod_database_code               4127102
_shelx_shelxl_version_number     2017/1
_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, 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
O1 O 0.62624(6) 1.0461(2) 0.4637(2) 0.0390(5) Uani 1 1 d . .
O2 O 0.61723(6) 0.7706(3) 0.29649(18) 0.0408(5) Uani 1 1 d . .
O3 O 0.63334(7) 0.5950(3) 0.45885(19) 0.0426(5) Uani 1 1 d . .
O4 O 0.47892(6) 0.6856(3) 0.5503(2) 0.0467(6) Uani 1 1 d . .
O5 O 0.79801(6) 0.9063(3) 0.6975(2) 0.0447(5) Uani 1 1 d . .
C1 C 0.61871(8) 0.9570(3) 0.5667(3) 0.0349(5) Uani 1 1 d . .
H1 H 0.631288 1.005385 0.649589 0.042 Uiso 1 1 calc R U
C2 C 0.64380(8) 0.8849(3) 0.4990(2) 0.0313(5) Uani 1 1 d . .
C3 C 0.62935(8) 0.7469(3) 0.4048(2) 0.0307(5) Uani 1 1 d . .
C4 C 0.62187(12) 0.4522(4) 0.3759(4) 0.0548(9) Uani 1 1 d . .
H4A H 0.636086 0.451348 0.314458 0.082 Uiso 1 1 calc R U
H4B H 0.595600 0.462937 0.333893 0.082 Uiso 1 1 calc R U
H4C H 0.626161 0.345831 0.423186 0.082 Uiso 1 1 calc R U
C5 C 0.58076(8) 0.8931(3) 0.5550(2) 0.0328(5) Uani 1 1 d . .
C6 C 0.57158(8) 0.8471(4) 0.6627(2) 0.0350(5) Uani 1 1 d . .
H6 H 0.589089 0.862309 0.740352 0.042 Uiso 1 1 calc R U
C7 C 0.53735(8) 0.7794(4) 0.6586(3) 0.0375(6) Uani 1 1 d . .
H7 H 0.531505 0.747844 0.732818 0.045 Uiso 1 1 calc R U
C8 C 0.51151(8) 0.7578(4) 0.5450(2) 0.0347(5) Uani 1 1 d . .
C9 C 0.51976(8) 0.8086(4) 0.4373(3) 0.0384(6) Uani 1 1 d . .
H9 H 0.501859 0.797746 0.360101 0.046 Uiso 1 1 calc R U
C10 C 0.55427(8) 0.8754(4) 0.4426(3) 0.0380(6) Uani 1 1 d . .
H10 H 0.559873 0.909456 0.368538 0.046 Uiso 1 1 calc R U
C11 C 0.45141(9) 0.6639(5) 0.4353(3) 0.0497(8) Uani 1 1 d . .
H11A H 0.461752 0.598360 0.378283 0.075 Uiso 1 1 calc R U
H11B H 0.443426 0.775791 0.399398 0.075 Uiso 1 1 calc R U
H11C H 0.430270 0.602748 0.449757 0.075 Uiso 1 1 calc R U
C12 C 0.68451(8) 0.8875(3) 0.5529(2) 0.0314(5) Uani 1 1 d . .
C13 C 0.70752(9) 0.9660(4) 0.4908(3) 0.0408(6) Uani 1 1 d . .
H13 H 0.697177 1.017362 0.412697 0.049 Uiso 1 1 calc R U
C14 C 0.74499(9) 0.9700(5) 0.5412(3) 0.0427(7) Uani 1 1 d . .
H14 H 0.760307 1.024829 0.498060 0.051 Uiso 1 1 calc R U
C15 C 0.76054(8) 0.8944(4) 0.6549(3) 0.0350(5) Uani 1 1 d . .
C16 C 0.73823(8) 0.8136(4) 0.7178(3) 0.0367(6) Uani 1 1 d . .
H16 H 0.748655 0.760903 0.795417 0.044 Uiso 1 1 calc R U
C17 C 0.70034(8) 0.8111(4) 0.6655(3) 0.0365(6) Uani 1 1 d . .
H17 H 0.684985 0.755648 0.708193 0.044 Uiso 1 1 calc R U
C18 C 0.81460(9) 0.8338(5) 0.8163(3) 0.0498(8) Uani 1 1 d . .
H18A H 0.808610 0.712184 0.815082 0.075 Uiso 1 1 calc R U
H18B H 0.805150 0.891415 0.878919 0.075 Uiso 1 1 calc R U
H18C H 0.841374 0.847971 0.836101 0.075 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0350
-1.00 0.00 0.00 0.0350
1.00 -2.00 -1.00 0.0600
0.00 1.00 0.00 0.0800
-3.00 -1.00 5.00 0.0850
1.00 -1.00 -4.00 0.0550
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C1 61.69(17)
C3 O3 C4 115.0(2)
C8 O4 C11 116.8(3)
C15 O5 C18 116.8(3)
O1 C1 C2 58.83(17)
O1 C1 C5 118.9(2)
C2 C1 C5 123.9(2)
O1 C2 C1 59.48(17)
O1 C2 C12 116.7(2)
C1 C2 C12 121.1(2)
O1 C2 C3 112.7(2)
C1 C2 C3 118.4(2)
C12 C2 C3 115.7(2)
O2 C3 O3 124.8(2)
O2 C3 C2 124.7(2)
O3 C3 C2 110.4(2)
C6 C5 C10 118.6(3)
C6 C5 C1 117.8(2)
C10 C5 C1 123.6(3)
C7 C6 C5 121.1(3)
C6 C7 C8 119.6(3)
O4 C8 C9 124.8(3)
O4 C8 C7 115.2(3)
C9 C8 C7 120.0(3)
C8 C9 C10 119.8(3)
C9 C10 C5 120.9(3)
C17 C12 C13 118.4(3)
C17 C12 C2 120.8(2)
C13 C12 C2 120.9(2)
C14 C13 C12 120.8(3)
C13 C14 C15 120.3(3)
O5 C15 C16 124.2(3)
O5 C15 C14 115.8(3)
C16 C15 C14 120.0(3)
C15 C16 C17 119.0(3)
C12 C17 C16 121.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.434(3)
O1 C1 1.444(4)
O2 C3 1.194(3)
O3 C3 1.329(3)
O3 C4 1.448(4)
O4 C8 1.369(4)
O4 C11 1.434(4)
O5 C15 1.368(3)
O5 C18 1.432(4)
C1 C2 1.476(4)
C1 C5 1.488(4)
C2 C12 1.492(4)
C2 C3 1.510(4)
C5 C6 1.392(4)
C5 C10 1.392(4)
C6 C7 1.384(4)
C7 C8 1.394(4)
C8 C9 1.385(4)
C9 C10 1.389(4)
C12 C17 1.383(4)
C12 C13 1.393(4)
C13 C14 1.374(4)
C14 C15 1.388(4)
C15 C16 1.388(4)
C16 C17 1.391(4)
