#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:18:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178621 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/32/4073229.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_4073229
loop_
_publ_author_name
'Bazinet, Patrick'
'Ong, Tiow-Gan'
'O'Brien, Julie S.'
'Lavoie, Nathalie'
'Bell, Eleanor'
'Yap, Glenn P. A.'
'Korobkov, Ilia'
'Richeson, Darrin S.'
_publ_section_title
;
 Design of Sterically Demanding, Electron-Rich Carbene Ligands with the
 Perimidine Scaffold
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2885
_journal_paper_doi               10.1021/om0701827
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C19 H24 N2'
_chemical_formula_weight         280.40
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                   11.1938(15)
_cell_length_b                   13.9491(19)
_cell_length_c                   10.5219(14)
_cell_measurement_reflns_used    583
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.33
_cell_volume                     1642.9(4)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11584
_diffrn_reflns_theta_full        24.74
_diffrn_reflns_theta_max         24.74
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2758
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.2058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                2230
_reflns_number_total             2758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0701827si20070227_100846.cif
_cod_data_source_block           dr59a
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               4073229
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
N1 N -0.03871(15) 0.79809(12) 0.82627(16) 0.0398(4) Uani 1 1 d .
N2 N 0.11470(14) 0.73522(12) 0.94432(16) 0.0384(4) Uani 1 1 d .
C1 C -0.08099(18) 0.85460(14) 0.92873(19) 0.0382(5) Uani 1 1 d .
C2 C -0.18432(19) 0.90926(15) 0.9231(2) 0.0456(5) Uani 1 1 d .
H2A H -0.2354 0.9053 0.8512 0.055 Uiso 1 1 calc R
C3 C -0.2129(2) 0.97098(16) 1.0252(2) 0.0508(6) Uani 1 1 d .
H3A H -0.2827 1.0096 1.0203 0.061 Uiso 1 1 calc R
C4 C -0.1424(2) 0.97616(16) 1.1303(2) 0.0496(6) Uani 1 1 d .
H4A H -0.1618 1.0201 1.1962 0.060 Uiso 1 1 calc R
C5 C -0.04134(19) 0.91720(15) 1.1426(2) 0.0440(6) Uani 1 1 d .
C6 C 0.0315(2) 0.91641(18) 1.2524(2) 0.0535(6) Uani 1 1 d .
H6A H 0.0124 0.9570 1.3220 0.064 Uiso 1 1 calc R
C7 C 0.1282(2) 0.85846(19) 1.2592(2) 0.0544(6) Uani 1 1 d .
H7A H 0.1756 0.8591 1.3341 0.065 Uiso 1 1 calc R
C8 C 0.1606(2) 0.79757(16) 1.1590(2) 0.0477(6) Uani 1 1 d .
H8A H 0.2296 0.7582 1.1657 0.057 Uiso 1 1 calc R
C9 C 0.09099(18) 0.79536(14) 1.05019(19) 0.0382(5) Uani 1 1 d .
C10 C -0.01015(19) 0.85593(15) 1.0393(2) 0.0378(5) Uani 1 1 d .
C11 C 0.0559(2) 0.73770(16) 0.8316(2) 0.0428(5) Uani 1 1 d .
C12 C -0.1085(2) 0.79929(17) 0.7060(2) 0.0488(6) Uani 1 1 d .
H12A H -0.1411 0.8655 0.6949 0.059 Uiso 1 1 calc R
C13 C -0.2140(2) 0.73109(18) 0.7162(3) 0.0661(7) Uani 1 1 d .
H13A H -0.2609 0.7468 0.7920 0.099 Uiso 1 1 calc R
H13B H -0.1847 0.6651 0.7227 0.099 Uiso 1 1 calc R
H13C H -0.2643 0.7374 0.6405 0.099 Uiso 1 1 calc R
C14 C -0.0315(2) 0.7772(2) 0.5910(2) 0.0650(7) Uani 1 1 d .
H14A H 0.0354 0.8224 0.5875 0.098 Uiso 1 1 calc R
H14B H -0.0796 0.7832 0.5136 0.098 Uiso 1 1 calc R
H14C H -0.0005 0.7117 0.5977 0.098 Uiso 1 1 calc R
C15 C 0.21181(17) 0.66413(15) 0.9510(2) 0.0420(5) Uani 1 1 d .
H15A H 0.2729 0.6879 1.0112 0.050 Uiso 1 1 calc R
H15B H 0.2499 0.6599 0.8662 0.050 Uiso 1 1 calc R
C16 C 0.17489(17) 0.56233(15) 0.9922(2) 0.0411(5) Uani 1 1 d .
C17 C 0.1020(2) 0.56246(17) 1.1149(2) 0.0478(6) Uani 1 1 d .
H17A H 0.1483 0.5932 1.1827 0.072 Uiso 1 1 calc R
H17B H 0.0835 0.4963 1.1393 0.072 Uiso 1 1 calc R
H17C H 0.0276 0.5980 1.1016 0.072 Uiso 1 1 calc R
C18 C 0.1020(2) 0.51348(18) 0.8876(2) 0.0572(6) Uani 1 1 d .
H18A H 0.0795 0.4489 0.9152 0.086 Uiso 1 1 calc R
H18B H 0.1500 0.5093 0.8099 0.086 Uiso 1 1 calc R
H18C H 0.0297 0.5510 0.8706 0.086 Uiso 1 1 calc R
C19 C 0.2901(2) 0.50612(19) 1.0109(3) 0.0683(8) Uani 1 1 d .
H19A H 0.3379 0.5365 1.0778 0.102 Uiso 1 1 calc R
H19B H 0.3356 0.5055 0.9313 0.102 Uiso 1 1 calc R
H19C H 0.2710 0.4402 1.0358 0.102 Uiso 1 1 calc R
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
C11 N1 C1 125.16(18)
C11 N1 C12 116.92(17)
C1 N1 C12 117.77(16)
C11 N2 C9 125.46(17)
C11 N2 C15 114.63(17)
C9 N2 C15 119.90(16)
C2 C1 C10 119.9(2)
C2 C1 N1 123.49(19)
C10 C1 N1 116.60(17)
C1 C2 C3 119.4(2)
C4 C3 C2 121.3(2)
C3 C4 C5 120.7(2)
C4 C5 C6 123.0(2)
C4 C5 C10 118.6(2)
C6 C5 C10 118.5(2)
C7 C6 C5 120.6(2)
C6 C7 C8 122.0(2)
C7 C8 C9 119.3(2)
C8 C9 N2 123.83(19)
C8 C9 C10 120.20(19)
N2 C9 C10 115.97(17)
C1 C10 C9 120.61(19)
C1 C10 C5 119.98(19)
C9 C10 C5 119.40(19)
N1 C11 N2 115.55(19)
N1 C12 C13 109.93(19)
N1 C12 C14 112.23(18)
C13 C12 C14 111.7(2)
N2 C15 C16 115.83(16)
C19 C16 C18 108.41(19)
C19 C16 C17 110.06(18)
C18 C16 C17 108.91(17)
C19 C16 C15 106.49(17)
C18 C16 C15 110.56(18)
C17 C16 C15 112.32(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.354(3)
N1 C1 1.417(3)
N1 C12 1.487(3)
N2 C11 1.357(3)
N2 C9 1.420(3)
N2 C15 1.473(2)
C1 C2 1.387(3)
C1 C10 1.408(3)
C2 C3 1.413(3)
C3 C4 1.361(3)
C4 C5 1.405(3)
C5 C6 1.415(3)
C5 C10 1.426(3)
C6 C7 1.353(3)
C7 C8 1.401(3)
C8 C9 1.385(3)
C9 C10 1.417(3)
C12 C13 1.520(3)
C12 C14 1.517(3)
C15 C16 1.541(3)
C16 C19 1.522(3)
C16 C18 1.530(3)
C16 C17 1.528(3)
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
C11 N1 C1 C2 -174.2(2)
C12 N1 C1 C2 1.1(3)
C11 N1 C1 C10 7.9(3)
C12 N1 C1 C10 -176.93(17)
C10 C1 C2 C3 4.4(3)
N1 C1 C2 C3 -173.52(18)
C1 C2 C3 C4 -1.5(3)
C2 C3 C4 C5 -2.6(3)
C3 C4 C5 C6 -176.9(2)
C3 C4 C5 C10 3.7(3)
C4 C5 C6 C7 -179.8(2)
C10 C5 C6 C7 -0.3(3)
C5 C6 C7 C8 0.2(3)
C6 C7 C8 C9 -0.9(3)
C7 C8 C9 N2 -178.9(2)
C7 C8 C9 C10 1.6(3)
C11 N2 C9 C8 -173.1(2)
C15 N2 C9 C8 5.5(3)
C11 N2 C9 C10 6.4(3)
C15 N2 C9 C10 -174.94(17)
C2 C1 C10 C9 175.47(18)
N1 C1 C10 C9 -6.5(3)
C2 C1 C10 C5 -3.2(3)
N1 C1 C10 C5 174.82(17)
C8 C9 C10 C1 179.62(19)
N2 C9 C10 C1 0.1(3)
C8 C9 C10 C5 -1.7(3)
N2 C9 C10 C5 178.80(18)
C4 C5 C10 C1 -0.8(3)
C6 C5 C10 C1 179.74(19)
C4 C5 C10 C9 -179.51(19)
C6 C5 C10 C9 1.0(3)
C1 N1 C11 N2 -2.1(3)
C12 N1 C11 N2 -177.32(18)
C9 N2 C11 N1 -5.4(3)
C15 N2 C11 N1 175.84(17)
C11 N1 C12 C13 94.2(2)
C1 N1 C12 C13 -81.4(2)
C11 N1 C12 C14 -30.8(3)
C1 N1 C12 C14 153.56(19)
C11 N2 C15 C16 -87.0(2)
C9 N2 C15 C16 94.2(2)
N2 C15 C16 C19 -171.91(19)
N2 C15 C16 C18 70.5(2)
N2 C15 C16 C17 -51.4(2)
