#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:45:11 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178914 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/43/4114318.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_4114318
loop_
_publ_author_name
'Patrick Bazinet'
'Glenn P. A. Yap'
'Darrin S. Richeson'
_publ_section_title
;
 Constructing a Stable Carbene with a Novel Topology and Electronic
 Framework
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13314
_journal_page_last               13315
_journal_paper_doi               10.1021/ja0372661
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C17 H20 N2'
_chemical_formula_weight         252.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 117.04(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.223(4)
_cell_length_b                   8.553(4)
_cell_length_c                   10.143(5)
_cell_measurement_reflns_used    2191
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.21
_cell_volume                     712.7(6)
_computing_cell_refinement       'SMART, Bruker (2000)'
_computing_data_collection       'SMART, Bruker (2000)'
_computing_data_reduction        'XPREP, Bruker (2000)'
_computing_molecular_graphics    'SHELXTL, Bruker (2000)'
_computing_publication_material  'SHELXTL, Bruker (2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.818
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_device_type  '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     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8330
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.86
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1986
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0759
_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)+(0.1800P)²+0.3031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2471
_refine_ls_wR_factor_ref         0.2596
_reflns_number_gt                1633
_reflns_number_total             3348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0372661si20030716_112519_1.cif
_cod_data_source_block           darr005
_cod_original_cell_volume        712.6(6)
_cod_database_code               4114318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
C1 C 0.7705(5) 0.9305(7) 0.1794(5) 0.0395(10) Uani 1 1 d .
C2 C 1.0088(4) 1.0959(7) 0.2684(6) 0.0472(13) Uani 1 1 d .
H2A H 1.0433 1.1835 0.2252 0.057 Uiso 1 1 calc R
C3 C 1.1524(6) 0.9874(9) 0.3417(8) 0.074(2) Uani 1 1 d .
H3A H 1.1808 0.9451 0.2677 0.111 Uiso 1 1 calc R
H3B H 1.1244 0.9025 0.3894 0.111 Uiso 1 1 calc R
H3C H 1.2444 1.0447 0.4152 0.111 Uiso 1 1 calc R
C4 C 0.9576(6) 1.1655(9) 0.3772(7) 0.0649(17) Uani 1 1 d .
H4A H 0.8671 1.2365 0.3258 0.097 Uiso 1 1 calc R
H4B H 1.0483 1.2223 0.4529 0.097 Uiso 1 1 calc R
H4C H 0.9244 1.0825 0.4229 0.097 Uiso 1 1 calc R
C5 C 0.8722(4) 1.0091(6) 0.0028(5) 0.0403(11) Uani 1 1 d .
C6 C 0.9896(6) 1.0818(7) -0.0272(7) 0.0538(14) Uani 1 1 d .
H6A H 1.0797 1.1311 0.0493 0.065 Uiso 1 1 calc R
C7 C 0.9725(7) 1.0808(8) -0.1725(8) 0.0652(17) Uani 1 1 d .
H7A H 1.0518 1.1311 -0.1913 0.078 Uiso 1 1 calc R
C8 C 0.8469(7) 1.0105(8) -0.2850(7) 0.0596(16) Uani 1 1 d .
H8A H 0.8384 1.0145 -0.3808 0.072 Uiso 1 1 calc R
C9 C 0.7253(6) 0.9291(7) -0.2597(6) 0.0476(13) Uani 1 1 d .
C10 C 0.7417(5) 0.9288(5) -0.1119(5) 0.0347(10) Uani 1 1 d .
C11 C 0.6270(4) 0.8468(6) -0.0812(5) 0.0364(10) Uani 1 1 d .
C12 C 0.4981(5) 0.7700(6) -0.1948(5) 0.0460(12) Uani 1 1 d .
H12A H 0.4213 0.7156 -0.1753 0.055 Uiso 1 1 calc R
C13 C 0.4828(6) 0.7741(8) -0.3407(6) 0.0580(15) Uani 1 1 d .
H13A H 0.3948 0.7228 -0.4176 0.070 Uiso 1 1 calc R
C14 C 0.5943(7) 0.8518(9) -0.3709(6) 0.0575(14) Uani 1 1 d .
H14A H 0.5819 0.8528 -0.4682 0.069 Uiso 1 1 calc R
C15 C 0.5378(5) 0.7584(6) 0.1065(5) 0.0413(11) Uani 1 1 d .
H15A H 0.5005 0.6661 0.0405 0.050 Uiso 1 1 calc R
C16 C 0.6210(7) 0.6981(8) 0.2641(6) 0.0637(17) Uani 1 1 d .
H16A H 0.7164 0.6380 0.2791 0.095 Uiso 1 1 calc R
H16B H 0.5463 0.6320 0.2820 0.095 Uiso 1 1 calc R
H16C H 0.6535 0.7857 0.3323 0.095 Uiso 1 1 calc R
C17 C 0.3874(7) 0.8590(8) 0.0730(9) 0.0689(19) Uani 1 1 d .
H17A H 0.3405 0.8947 -0.0288 0.103 Uiso 1 1 calc R
H17B H 0.4188 0.9485 0.1389 0.103 Uiso 1 1 calc R
H17C H 0.3077 0.7973 0.0877 0.103 Uiso 1 1 calc R
N1 N 0.8725(4) 1.0118(5) 0.1419(4) 0.0385(9) Uani 1 1 d .
N2 N 0.6528(4) 0.8470(5) 0.0677(4) 0.0358(9) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 N2 115.3(4)
C4 C2 N1 113.2(3)
C4 C2 C3 112.3(5)
N1 C2 C3 109.3(5)
C6 C5 N1 124.2(5)
C6 C5 C10 119.4(5)
N1 C5 C10 116.4(4)
C5 C6 C7 119.7(5)
C8 C7 C6 122.3(5)
C7 C8 C9 120.4(5)
C14 C9 C10 119.1(5)
C14 C9 C8 123.1(5)
C10 C9 C8 117.8(5)
C11 C10 C5 120.0(4)
C11 C10 C9 119.7(4)
C5 C10 C9 120.3(4)
C12 C11 C10 119.7(4)
C12 C11 N2 123.4(4)
C10 C11 N2 116.9(4)
C11 C12 C13 119.7(5)
C14 C13 C12 121.0(5)
C13 C14 C9 120.9(5)
N2 C15 C16 111.8(3)
N2 C15 C17 109.7(4)
C16 C15 C17 113.4(5)
C1 N1 C5 125.9(4)
C1 N1 C2 115.0(4)
C5 N1 C2 118.7(4)
C1 N2 C11 124.9(4)
C1 N2 C15 116.1(3)
C11 N2 C15 118.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.355(6)
C1 N2 1.362(6)
C2 C4 1.506(8)
C2 N1 1.509(6)
C2 C3 1.508(8)
C5 C6 1.397(6)
C5 N1 1.410(6)
C5 C10 1.414(6)
C6 C7 1.409(9)
C7 C8 1.343(9)
C8 C9 1.438(8)
C9 C14 1.390(9)
C9 C10 1.436(7)
C10 C11 1.418(6)
C11 C12 1.388(6)
C11 N2 1.418(6)
C12 C13 1.422(8)
C13 C14 1.371(9)
C15 N2 1.495(5)
C15 C16 1.515(8)
C15 C17 1.533(8)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C5 C6 C7 -175.9(5)
C10 C5 C6 C7 3.1(8)
C5 C6 C7 C8 -0.7(9)
C6 C7 C8 C9 -1.5(10)
C7 C8 C9 C14 -178.8(5)
C7 C8 C9 C10 1.2(8)
C6 C5 C10 C11 176.3(4)
N1 C5 C10 C11 -4.6(6)
C6 C5 C10 C9 -3.4(6)
N1 C5 C10 C9 175.7(4)
C14 C9 C10 C11 1.6(7)
C8 C9 C10 C11 -178.4(5)
C14 C9 C10 C5 -178.8(5)
C8 C9 C10 C5 1.2(7)
C5 C10 C11 C12 179.1(4)
C9 C10 C11 C12 -1.2(6)
C5 C10 C11 N2 -1.5(6)
C9 C10 C11 N2 178.1(4)
C10 C11 C12 C13 0.2(7)
N2 C11 C12 C13 -179.1(5)
C11 C12 C13 C14 0.5(8)
C12 C13 C14 C9 -0.2(9)
C10 C9 C14 C13 -0.9(9)
C8 C9 C14 C13 179.1(5)
N2 C1 N1 C5 -3.9(7)
N2 C1 N1 C2 -176.4(4)
C6 C5 N1 C1 -173.1(5)
C10 C5 N1 C1 7.8(6)
C6 C5 N1 C2 -0.9(7)
C10 C5 N1 C2 -180.0(4)
C4 C2 N1 C1 -37.9(7)
C3 C2 N1 C1 88.1(5)
C4 C2 N1 C5 149.1(5)
C3 C2 N1 C5 -84.9(6)
N1 C1 N2 C11 -3.3(7)
N1 C1 N2 C15 -179.2(4)
C12 C11 N2 C1 -174.8(5)
C10 C11 N2 C1 5.9(6)
C12 C11 N2 C15 1.0(7)
C10 C11 N2 C15 -178.3(4)
C16 C15 N2 C1 -33.9(6)
C17 C15 N2 C1 92.8(5)
C16 C15 N2 C11 149.9(5)
C17 C15 N2 C11 -83.4(5)
