#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:21:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178505 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/70/4067003.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_4067003
loop_
_publ_author_name
'Hudnall, Todd W.'
'Tennyson, Andrew G.'
'Bielawski, Christopher W.'
_publ_section_title
;
 A Seven-MemberedN,N′-Diamidocarbene
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              4569
_journal_paper_doi               10.1021/om1007665
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C27 H26 N2 O2 - C6H6'
_chemical_formula_sum            'C33 H32 N2 O2'
_chemical_formula_weight         488.61
_chemical_name_common            7-KetoMes-carbene
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1242(6)
_cell_length_b                   14.8492(9)
_cell_length_c                   20.9679(13)
_cell_measurement_temperature    150(2)
_cell_volume                     2840.9(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku mini CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23860
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0789P)²+0.7192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                2097
_reflns_number_total             2600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1007665_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4067003
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.05194(13) 0.17010(8) 0.38709(6) 0.0279(3) Uani 1 1 d . .
O1 O -0.11558(13) 0.06241(8) 0.36682(7) 0.0481(4) Uani 1 1 d . .
C6 C 0.15637(16) 0.09487(10) 0.38992(7) 0.0316(4) Uani 1 1 d . .
C1 C 0.1222(2) 0.2500 0.39253(10) 0.0292(5) Uani 1 2 d S .
C3 C -0.22221(15) 0.20265(10) 0.38830(7) 0.0300(4) Uani 1 1 d . .
C7 C 0.21871(18) 0.06356(11) 0.33361(9) 0.0415(4) Uani 1 1 d . .
C2 C -0.09559(16) 0.14103(10) 0.37899(7) 0.0308(4) Uani 1 1 d . .
C11 C 0.19354(17) 0.06068(10) 0.44945(8) 0.0375(4) Uani 1 1 d . .
C4 C -0.35576(17) 0.15785(13) 0.39577(8) 0.0419(4) Uani 1 1 d . .
H4A H -0.3572 0.0952 0.3950 0.050 Uiso 1 1 calc R .
C8 C 0.3235(2) -0.00439(12) 0.33870(10) 0.0537(5) Uani 1 1 d . .
H8A H 0.3672 -0.0263 0.3017 0.064 Uiso 1 1 calc R .
C10 C 0.2990(2) -0.00733(12) 0.45119(10) 0.0516(5) Uani 1 1 d . .
H10A H 0.3258 -0.0312 0.4905 0.062 Uiso 1 1 calc R .
C14 C 0.1269(2) 0.09753(13) 0.50943(9) 0.0514(5) Uani 1 1 d . .
H14A H 0.0221 0.0981 0.5054 0.077 Uiso 1 1 calc R .
H14B H 0.1616 0.1578 0.5164 0.077 Uiso 1 1 calc R .
H14C H 0.1544 0.0603 0.5449 0.077 Uiso 1 1 calc R .
C5 C -0.48488(18) 0.20365(13) 0.40416(10) 0.0507(5) Uani 1 1 d . .
H5A H -0.5721 0.1722 0.4098 0.061 Uiso 1 1 calc R .
C9 C 0.3649(2) -0.04040(13) 0.39687(11) 0.0564(6) Uani 1 1 d . .
C12 C 0.1760(3) 0.10187(16) 0.27008(9) 0.0651(6) Uani 1 1 d . .
H12A H 0.2068 0.1636 0.2676 0.098 Uiso 1 1 calc R .
H12B H 0.0715 0.0986 0.2652 0.098 Uiso 1 1 calc R .
H12C H 0.2222 0.0679 0.2367 0.098 Uiso 1 1 calc R .
C13 C 0.4796(3) -0.11459(17) 0.40009(17) 0.0961(10) Uani 1 1 d . .
H13A H 0.4608 -0.1582 0.3673 0.144 Uiso 1 1 calc R .
H13B H 0.4752 -0.1434 0.4410 0.144 Uiso 1 1 calc R .
H13C H 0.5752 -0.0890 0.3940 0.144 Uiso 1 1 calc R .
C200 C 0.1674(6) 0.2044(3) 0.7097(3) 0.0883(13) Uani 0.70 1 d PU 1
H20A H 0.2415 0.1728 0.7303 0.106 Uiso 0.70 1 calc PR 1
C201 C 0.0602(8) 0.1604(4) 0.6798(3) 0.0800(15) Uani 0.70 1 d PU 1
H20E H 0.0602 0.0978 0.6799 0.096 Uiso 0.70 1 calc PR 1
C202 C -0.0477(6) 0.2045(4) 0.6496(3) 0.0818(16) Uani 0.70 1 d PU 1
H20B H -0.1216 0.1728 0.6288 0.098 Uiso 0.70 1 calc PR 1
C300 C 0.2094(15) 0.2500 0.6964(6) 0.059(3) Uani 0.30 2 d SPU 2
H30A H 0.3033 0.2500 0.7136 0.071 Uiso 0.30 2 calc SPR 2
C301 C -0.069(2) 0.2500 0.6431(11) 0.071(4) Uani 0.30 2 d SPU 2
H30B H -0.1612 0.2500 0.6238 0.085 Uiso 0.30 2 calc SPR 2
C302 C -0.0039(14) 0.1667(8) 0.6569(6) 0.060(2) Uani 0.30 1 d PU 2
H30C H -0.0531 0.1131 0.6489 0.072 Uiso 0.30 1 calc PR 2
C304 C 0.1391(12) 0.1663(8) 0.6834(6) 0.059(2) Uani 0.30 1 d PU 2
H30D H 0.1862 0.1122 0.6923 0.070 Uiso 0.30 1 calc PR 2
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'
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
C1 N1 C2 136.35(13) . .
C1 N1 C6 110.85(12) . .
C2 N1 C6 112.79(12) . .
C11 C6 C7 122.73(15) . .
C11 C6 N1 118.18(13) . .
C7 C6 N1 119.02(14) . .
N1 C1 N1 122.50(18) . 8_565
C4 C3 C3 118.43(10) . 8_565
C4 C3 C2 113.55(14) . .
C3 C3 C2 127.99(8) 8_565 .
C6 C7 C8 117.23(17) . .
C6 C7 C12 121.39(16) . .
C8 C7 C12 121.38(17) . .
O1 C2 N1 117.43(14) . .
O1 C2 C3 120.32(14) . .
N1 C2 C3 122.17(13) . .
C6 C11 C10 117.14(16) . .
C6 C11 C14 121.38(14) . .
C10 C11 C14 121.44(16) . .
C5 C4 C3 121.83(17) . .
C5 C4 H4A 119.1 . .
C3 C4 H4A 119.1 . .
C9 C8 C7 122.26(18) . .
C9 C8 H8A 118.9 . .
C7 C8 H8A 118.9 . .
C9 C10 C11 122.48(18) . .
C9 C10 H10A 118.8 . .
C11 C10 H10A 118.8 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C4 C5 C5 119.72(11) . 8_565
C4 C5 H5A 120.1 . .
C5 C5 H5A 120.1 8_565 .
C10 C9 C8 118.15(17) . .
C10 C9 C13 121.4(2) . .
C8 C9 C13 120.4(2) . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C201 C200 C200 119.4(3) . 8_565
C201 C200 H20A 120.3 . .
C200 C200 H20A 120.3 8_565 .
C200 C201 C202 121.5(5) . .
C200 C201 H20E 119.3 . .
C202 C201 H20E 119.3 . .
C201 C202 C202 119.2(4) . 8_565
C201 C202 H20B 120.4 . .
C202 C202 H20B 120.4 8_565 .
C304 C300 C304 121.5(14) . 8_565
C304 C300 H30A 119.3 . .
C304 C300 H30A 119.3 8_565 .
C302 C301 C302 123(2) 8_565 .
C302 C301 H30B 118.3 8_565 .
C302 C301 H30B 118.3 . .
C304 C302 C301 118.5(15) . .
C304 C302 H30C 120.8 . .
C301 C302 H30C 120.8 . .
C302 C304 C300 119.0(11) . .
C302 C304 H30D 120.5 . .
C300 C304 H30D 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3534(16) .
N1 C2 1.4238(19) .
N1 C6 1.4695(19) .
O1 C2 1.2089(18) .
C6 C11 1.390(2) .
C6 C7 1.391(2) .
C1 N1 1.3534(16) 8_565
C3 C4 1.397(2) .
C3 C3 1.406(3) 8_565
C3 C2 1.487(2) .
C7 C8 1.394(3) .
C7 C12 1.500(3) .
C11 C10 1.395(2) .
C11 C14 1.500(3) .
C4 C5 1.372(2) .
C4 H4A 0.9300 .
C8 C9 1.384(3) .
C8 H8A 0.9300 .
C10 C9 1.378(3) .
C10 H10A 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C5 C5 1.376(4) 8_565
C5 H5A 0.9300 .
C9 C13 1.521(3) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C200 C201 1.332(7) .
C200 C200 1.355(10) 8_565
C200 H20A 0.9300 .
C201 C202 1.342(7) .
C201 H20E 0.9300 .
C202 C202 1.352(11) 8_565
C202 H20B 0.9300 .
C300 C304 1.424(15) .
C300 C304 1.424(15) 8_565
C300 H30A 0.9300 .
C301 C302 1.403(17) 8_565
C301 C302 1.403(17) .
C301 H30B 0.9300 .
C302 C304 1.418(16) .
C302 H30C 0.9300 .
C304 H30D 0.9300 .
