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#$Date: 2016-03-22 11:25:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178898 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/27/4112749.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_4112749
loop_
_publ_author_name
'Vincent Lavallo'
'John Mafhouz'
'Yves Canac'
'Bruno Donnadieu'
'Wolfgand W. Schoeller'
_publ_contact_author             'Prof Guy Bertrand'
_publ_contact_author_address
;
UCR-CNRS
Joint Research Chemistry
Laboratory
University of California
(UMR 2282)
University of California
Riverside, CA 92521 USA
;
_publ_contact_author_email       ' gbertrand@maill.ucr.edu  '
_publ_contact_author_fax         '(909) 787 4713'
_publ_section_title
;
 Synthesis, Reactivity, and Ligand Properties of a Stable Alkyl Carbene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8670
_journal_page_last               8671
_journal_paper_doi               10.1021/ja047503f
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C5.5 H11.5 N0.5'
_chemical_formula_weight         84.65
_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            8
_cell_length_a                   15.7564(6)
_cell_length_b                   10.8550(9)
_cell_length_c                   6.9155(12)
_cell_measurement_temperature    223(2)
_cell_volume                     1182.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8359
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.951
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         1537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0874P)²+0.1486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                1239
_reflns_number_total             1537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja047503fsi20040429_013312_2.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      ' P n m a'
_cod_database_code               4112749
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
N1 N 0.10221(6) 0.2500 0.66936(15) 0.0268(3) Uani 1 2 d S
C1 C 0.05227(8) 0.2500 0.52016(19) 0.0322(3) Uani 1 2 d S
C2 C -0.04472(8) 0.2500 0.5466(2) 0.0380(4) Uani 1 2 d S
C3 C -0.08153(11) 0.2500 0.3402(3) 0.0783(8) Uani 1 2 d S
H3A H -0.1429 0.2562 0.3465 0.117 Uiso 0.50 1 calc PR
H3B H -0.0659 0.1742 0.2752 0.117 Uiso 0.50 1 calc PR
H3C H -0.0590 0.3197 0.2689 0.117 Uiso 0.50 1 calc PR
C4 C -0.07767(7) 0.36702(11) 0.6469(2) 0.0504(4) Uani 1 1 d .
H4A H -0.0637 0.3638 0.7834 0.076 Uiso 1 1 calc R
H4B H -0.1388 0.3722 0.6315 0.076 Uiso 1 1 calc R
H4C H -0.0513 0.4388 0.5890 0.076 Uiso 1 1 calc R
C5 C 0.19624(8) 0.2500 0.62785(19) 0.0319(3) Uani 1 2 d S
H5 H 0.2263 0.2500 0.7536 0.038 Uiso 1 2 calc SR
C6 C 0.22143(7) 0.13364(11) 0.52121(18) 0.0486(3) Uani 1 1 d .
H6A H 0.1916 0.1299 0.3986 0.073 Uiso 1 1 calc R
H6B H 0.2066 0.0623 0.5987 0.073 Uiso 1 1 calc R
H6C H 0.2821 0.1342 0.4981 0.073 Uiso 1 1 calc R
C7 C 0.08149(9) 0.2500 0.88157(19) 0.0346(3) Uani 1 2 d S
H7 H 0.0189 0.2500 0.8930 0.041 Uiso 1 2 calc SR
C8 C 0.11345(9) 0.13369(13) 0.98013(18) 0.0544(4) Uani 1 1 d .
H8A H 0.0913 0.0620 0.9133 0.082 Uiso 1 1 calc R
H8B H 0.0945 0.1327 1.1136 0.082 Uiso 1 1 calc R
H8C H 0.1750 0.1321 0.9764 0.082 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0238(5) 0.0308(5) 0.0256(5) 0.000 0.0004(4) 0.000
C1 0.0234(6) 0.0437(7) 0.0294(6) 0.000 -0.0013(5) 0.000
C2 0.0216(6) 0.0533(9) 0.0392(7) 0.000 -0.0001(5) 0.000
C3 0.0308(8) 0.154(3) 0.0503(11) 0.000 -0.0140(7) 0.000
C4 0.0315(5) 0.0431(6) 0.0765(9) 0.0077(5) 0.0056(5) 0.0072(4)
C5 0.0229(6) 0.0421(7) 0.0306(6) 0.000 -0.0028(5) 0.000
C6 0.0297(5) 0.0606(7) 0.0553(7) -0.0169(5) 0.0001(4) 0.0088(4)
C7 0.0364(7) 0.0425(8) 0.0248(6) 0.000 0.0016(5) 0.000
C8 0.0592(8) 0.0630(8) 0.0411(6) 0.0208(5) -0.0009(5) 0.0051(6)
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'
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 C7 130.13(11) . .
C1 N1 C5 116.36(11) . .
C7 N1 C5 113.51(10) . .
N1 C1 C2 120.50(12) . .
C4 C2 C4 111.42(13) 8_565 .
C4 C2 C1 112.88(7) 8_565 .
C4 C2 C1 112.88(7) . .
C4 C2 C3 106.90(9) 8_565 .
C4 C2 C3 106.90(9) . .
C1 C2 C3 105.29(12) . .
N1 C5 C6 110.46(7) . .
N1 C5 C6 110.46(7) . 8_565
C6 C5 C6 112.91(13) . 8_565
N1 C7 C8 111.45(8) . 8_565
N1 C7 C8 111.45(8) . .
C8 C7 C8 112.26(14) 8_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.2976(17) .
N1 C7 1.5034(16) .
N1 C5 1.5091(16) .
C1 C2 1.5392(18) .
C2 C4 1.5375(15) 8_565
C2 C4 1.5375(15) .
C2 C3 1.541(2) .
C5 C6 1.5155(13) .
C5 C6 1.5155(13) 8_565
C7 C8 1.5206(14) 8_565
C7 C8 1.5206(14) .
