#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:28:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180183 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/79/7107965.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_7107965
loop_
_publ_author_name
'Gael Ung'
'Daniel Mendoza-Espinosa'
'Guy Bertrand'
_publ_section_title
;
 Ynamides: stable ligand equivalents of unstable oxazol-4-ylidenes (novel
 mesoionic carbenes)
;
_journal_name_full               Chem.Commun.
_journal_page_first              7088
_journal_paper_doi               10.1039/c2cc33319h
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C20 H17 Cl N O3 Rh, C H Cl3'
_chemical_formula_sum            'C21 H18 Cl4 N O3 Rh'
_chemical_formula_weight         577.07
_chemical_name_common            GU1188
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.668(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7427(9)
_cell_length_b                   19.1083(12)
_cell_length_c                   8.2340(5)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.84
_cell_measurement_theta_min      3.27
_cell_volume                     2318.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33043
_diffrn_reflns_theta_full        41.65
_diffrn_reflns_theta_max         41.65
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.028
_refine_diff_density_min         -1.808
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         14858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.5613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                10254
_reflns_number_total             14858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc33319h.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7107965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Rh1 Rh 0.705169(8) 0.507310(6) 0.575984(14) 0.01836(3) Uani 1 1 d .
Cl1 Cl 0.82546(3) 0.47547(2) 0.40494(5) 0.02190(7) Uani 1 1 d .
O1 O 0.78962(8) 0.72139(6) 0.54741(13) 0.01762(17) Uani 1 1 d .
O2 O 0.55611(12) 0.55298(10) 0.7855(2) 0.0435(4) Uani 1 1 d .
O3 O 0.61942(15) 0.36422(8) 0.5283(3) 0.0464(4) Uani 1 1 d .
N1 N 0.83089(9) 0.63297(6) 0.69674(15) 0.01680(19) Uani 1 1 d .
C1 C 0.75881(10) 0.60745(7) 0.59569(17) 0.0177(2) Uani 1 1 d .
C2 C 0.73450(10) 0.66446(7) 0.50488(17) 0.0178(2) Uani 1 1 d .
C3 C 0.84779(10) 0.69923(7) 0.66214(17) 0.0168(2) Uani 1 1 d .
C4 C 0.87603(11) 0.59453(8) 0.83426(18) 0.0198(2) Uani 1 1 d .
H4 H 0.9113 0.6285 0.8990 0.024 Uiso 1 1 calc R
C5 C 0.94153(14) 0.54049(10) 0.7713(2) 0.0285(3) Uani 1 1 d .
H5A H 0.9086 0.5063 0.7077 0.043 Uiso 1 1 calc R
H5B H 0.9721 0.5178 0.8614 0.043 Uiso 1 1 calc R
H5C H 0.9853 0.5631 0.7051 0.043 Uiso 1 1 calc R
C6 C 0.80555(13) 0.56271(10) 0.9433(2) 0.0264(3) Uani 1 1 d .
H6A H 0.7628 0.5981 0.9729 0.040 Uiso 1 1 calc R
H6B H 0.8351 0.5443 1.0396 0.040 Uiso 1 1 calc R
H6C H 0.7743 0.5257 0.8863 0.040 Uiso 1 1 calc R
C7 C 0.91548(10) 0.74802(7) 0.72701(17) 0.0173(2) Uani 1 1 d .
C8 C 0.89087(11) 0.81857(8) 0.74093(18) 0.0191(2) Uani 1 1 d .
H8 H 0.8333 0.8331 0.7065 0.023 Uiso 1 1 calc R
C9 C 0.95226(12) 0.86669(8) 0.8059(2) 0.0235(3) Uani 1 1 d .
H9 H 0.9356 0.9134 0.8163 0.028 Uiso 1 1 calc R
C10 C 1.03852(13) 0.84516(9) 0.8554(2) 0.0261(3) Uani 1 1 d .
H10 H 1.0793 0.8773 0.9006 0.031 Uiso 1 1 calc R
C11 C 1.06410(12) 0.77573(10) 0.8376(2) 0.0276(3) Uani 1 1 d .
H11 H 1.1224 0.7617 0.8690 0.033 Uiso 1 1 calc R
C12 C 1.00316(11) 0.72714(9) 0.7732(2) 0.0232(3) Uani 1 1 d .
H12 H 1.0207 0.6807 0.7608 0.028 Uiso 1 1 calc R
C13 C 0.66409(10) 0.67748(8) 0.38089(17) 0.0187(2) Uani 1 1 d .
C14 C 0.62488(12) 0.62144(9) 0.2945(2) 0.0239(3) Uani 1 1 d .
H14 H 0.6471 0.5763 0.3104 0.029 Uiso 1 1 calc R
C15 C 0.55293(13) 0.63312(10) 0.1852(2) 0.0277(3) Uani 1 1 d .
H15 H 0.5269 0.5957 0.1287 0.033 Uiso 1 1 calc R
C16 C 0.51954(12) 0.70037(11) 0.1598(2) 0.0277(3) Uani 1 1 d .
H16 H 0.4702 0.7078 0.0889 0.033 Uiso 1 1 calc R
C17 C 0.56031(13) 0.75621(10) 0.2406(2) 0.0263(3) Uani 1 1 d .
H17 H 0.5392 0.8014 0.2213 0.032 Uiso 1 1 calc R
C18 C 0.63219(11) 0.74535(8) 0.34999(19) 0.0217(3) Uani 1 1 d .
H18 H 0.6593 0.7833 0.4030 0.026 Uiso 1 1 calc R
C19 C 0.61322(13) 0.53514(10) 0.7050(2) 0.0282(3) Uani 1 1 d .
C20 C 0.65241(13) 0.41701(9) 0.5473(2) 0.0276(3) Uani 1 1 d .
C21 C 0.26909(12) 0.87109(9) 0.3882(2) 0.0247(3) Uani 1 1 d .
H21 H 0.2336 0.8891 0.2949 0.030 Uiso 1 1 calc R
Cl2 Cl 0.35839(3) 0.92918(3) 0.43036(7) 0.03717(10) Uani 1 1 d .
Cl3 Cl 0.19697(5) 0.86428(3) 0.55413(8) 0.04449(14) Uani 1 1 d .
Cl4 Cl 0.31110(4) 0.78830(3) 0.33714(8) 0.04242(12) Uani 1 1 d .
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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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
C19 Rh1 C20 91.63(8)
C19 Rh1 C1 88.49(7)
C20 Rh1 C1 176.85(7)
C19 Rh1 Cl1 177.88(6)
C20 Rh1 Cl1 90.21(5)
C1 Rh1 Cl1 89.61(4)
C3 O1 C2 106.83(11)
C3 N1 C1 110.22(12)
C3 N1 C4 123.54(13)
C1 N1 C4 125.97(12)
C2 C1 N1 103.16(12)
C2 C1 Rh1 126.90(11)
N1 C1 Rh1 129.85(10)
C1 C2 O1 110.07(13)
C1 C2 C13 133.77(14)
O1 C2 C13 116.14(12)
N1 C3 O1 109.68(13)
N1 C3 C7 131.70(13)
O1 C3 C7 118.62(12)
N1 C4 C5 110.54(12)
N1 C4 C6 110.38(13)
C5 C4 C6 112.50(14)
C12 C7 C8 119.53(14)
C12 C7 C3 122.46(13)
C8 C7 C3 118.01(13)
C9 C8 C7 120.12(15)
C8 C9 C10 119.96(15)
C9 C10 C11 120.15(16)
C12 C11 C10 120.35(17)
C11 C12 C7 119.84(15)
C18 C13 C14 118.96(14)
C18 C13 C2 120.96(14)
C14 C13 C2 120.04(14)
C15 C14 C13 120.14(16)
C14 C15 C16 120.46(17)
C17 C16 C15 119.52(16)
C16 C17 C18 120.64(16)
C17 C18 C13 120.20(16)
O2 C19 Rh1 179.50(18)
O3 C20 Rh1 178.3(2)
Cl2 C21 Cl4 110.54(10)
Cl2 C21 Cl3 111.18(10)
Cl4 C21 Cl3 110.18(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Rh1 C19 1.8256(19)
Rh1 C20 1.9046(18)
Rh1 C1 2.0750(14)
Rh1 Cl1 2.3757(4)
O1 C3 1.3266(18)
O1 C2 1.3962(18)
O2 C19 1.139(2)
O3 C20 1.129(2)
N1 C3 1.3232(18)
N1 C1 1.4169(19)
N1 C4 1.4902(19)
C1 C2 1.363(2)
C2 C13 1.456(2)
C3 C7 1.456(2)
C4 C5 1.515(2)
C4 C6 1.520(2)
C7 C12 1.395(2)
C7 C8 1.402(2)
C8 C9 1.387(2)
C9 C10 1.387(3)
C10 C11 1.388(3)
C11 C12 1.387(2)
C13 C18 1.400(2)
C13 C14 1.401(2)
C14 C15 1.389(2)
C15 C16 1.390(3)
C16 C17 1.385(3)
C17 C18 1.386(2)
C21 Cl2 1.7491(18)
C21 Cl4 1.7546(18)
C21 Cl3 1.7599(18)
