#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/63/4076338.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_4076338
loop_
_publ_author_name
'Tan, Runyu'
'Chiu, Frederick Sin Nang'
'Hadzovic, Alen'
'Song, Datong'
_publ_section_title
;
 Construction of Rhodium(I) and Gold(I) Macrocycles by Transferring a
 Phosphine-Functionalized 4,5-Diazafluorenide Ligand from Its Copper(I)
 N-Heterocyclic Carbene Complex
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              2184
_journal_paper_doi               10.1021/om200994b
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C13 H10 N2'
_chemical_formula_sum            'C13 H10 N2'
_chemical_formula_weight         194.23
_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                 101.579(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.434(2)
_cell_length_b                   10.147(3)
_cell_length_c                   12.988(3)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.57
_cell_volume                     959.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7972
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.9896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX 2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0403
_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)+(0.0545P)²+0.1343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                1593
_reflns_number_total             2187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200994b_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'P 21/c'
_cod_database_code               4076338
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
C1 C 0.30924(19) 0.11287(15) 0.00771(11) 0.0305(3) Uani 1 1 d .
H1A H 0.3217 0.0326 0.0462 0.037 Uiso 1 1 calc R
C2 C 0.30920(18) 0.10624(14) -0.09941(11) 0.0301(3) Uani 1 1 d .
H2A H 0.3197 0.0234 -0.1317 0.036 Uiso 1 1 calc R
C3 C 0.29381(17) 0.22058(14) -0.15880(11) 0.0273(3) Uani 1 1 d .
H3A H 0.2946 0.2189 -0.2318 0.033 Uiso 1 1 calc R
C4 C 0.27734(16) 0.33720(13) -0.10661(10) 0.0230(3) Uani 1 1 d .
C5 C 0.27642(16) 0.33388(14) 0.00169(10) 0.0229(3) Uani 1 1 d .
C6 C 0.24789(16) 0.46898(14) 0.03617(10) 0.0230(3) Uani 1 1 d .
C7 C 0.23505(16) 0.55309(14) -0.05101(10) 0.0236(3) Uani 1 1 d .
C8 C 0.20505(19) 0.68555(14) -0.03801(11) 0.0303(3) Uani 1 1 d .
H8A H 0.1958 0.7458 -0.0948 0.036 Uiso 1 1 calc R
C9 C 0.18897(19) 0.72743(15) 0.06162(11) 0.0327(4) Uani 1 1 d .
H9A H 0.1687 0.8179 0.0743 0.039 Uiso 1 1 calc R
C10 C 0.20260(18) 0.63651(14) 0.14206(11) 0.0300(3) Uani 1 1 d .
H10A H 0.1903 0.6681 0.2091 0.036 Uiso 1 1 calc R
C11 C 0.25271(17) 0.47496(14) -0.14461(10) 0.0243(3) Uani 1 1 d .
C12 C 0.34568(18) 0.52971(16) -0.23009(10) 0.0304(3) Uani 1 1 d .
H12A H 0.3914 0.6215 -0.2223 0.036 Uiso 1 1 calc R
H12B H 0.4217 0.4686 -0.2627 0.036 Uiso 1 1 calc R
C13 C 0.14316(18) 0.50913(15) -0.25362(11) 0.0304(4) Uani 1 1 d .
H13A H 0.0941 0.4353 -0.3008 0.037 Uiso 1 1 calc R
H13B H 0.0637 0.5883 -0.2604 0.037 Uiso 1 1 calc R
N1 N 0.29297(15) 0.22454(11) 0.06042(9) 0.0275(3) Uani 1 1 d .
N2 N 0.23185(14) 0.50711(11) 0.13266(9) 0.0267(3) 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 C2 124.65(13)
C3 C2 C1 119.94(13)
C4 C3 C2 116.73(13)
C3 C4 C5 119.23(12)
C3 C4 C11 131.45(12)
C5 C4 C11 109.29(12)
N1 C5 C4 124.81(12)
N1 C5 C6 126.99(12)
C4 C5 C6 108.16(11)
N2 C6 C7 125.02(13)
N2 C6 C5 126.83(12)
C7 C6 C5 108.14(11)
C8 C7 C6 118.68(13)
C8 C7 C11 131.80(13)
C6 C7 C11 109.50(12)
C7 C8 C9 117.29(13)
C10 C9 C8 119.52(14)
N2 C10 C9 125.00(13)
C7 C11 C4 104.91(11)
C7 C11 C13 121.49(12)
C4 C11 C13 122.08(12)
C7 C11 C12 122.07(12)
C4 C11 C12 122.84(12)
C13 C11 C12 58.47(9)
C13 C12 C11 60.75(9)
C12 C13 C11 60.78(9)
C5 N1 C1 114.63(12)
C6 N2 C10 114.50(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3418(18)
C1 C2 1.393(2)
C2 C3 1.385(2)
C3 C4 1.3813(19)
C4 C5 1.4084(19)
C4 C11 1.4816(19)
C5 N1 1.3380(17)
C5 C6 1.4707(19)
C6 N2 1.3396(17)
C6 C7 1.4058(19)
C7 C8 1.378(2)
C7 C11 1.4792(19)
C8 C9 1.390(2)
C9 C10 1.382(2)
C10 N2 1.3404(18)
C11 C13 1.5248(19)
C11 C12 1.5253(18)
C12 C13 1.4896(19)
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 C1 C2 C3 0.8(2)
C1 C2 C3 C4 -0.58(19)
C2 C3 C4 C5 -0.22(18)
C2 C3 C4 C11 -177.81(13)
C3 C4 C5 N1 0.94(19)
C11 C4 C5 N1 179.03(11)
C3 C4 C5 C6 -177.10(11)
C11 C4 C5 C6 0.99(14)
N1 C5 C6 N2 -0.5(2)
C4 C5 C6 N2 177.43(11)
N1 C5 C6 C7 -179.00(12)
C4 C5 C6 C7 -1.02(14)
N2 C6 C7 C8 0.51(19)
C5 C6 C7 C8 178.99(11)
N2 C6 C7 C11 -177.84(11)
C5 C6 C7 C11 0.64(13)
C6 C7 C8 C9 -0.13(18)
C11 C7 C8 C9 177.79(12)
C7 C8 C9 C10 -0.27(19)
C8 C9 C10 N2 0.4(2)
C8 C7 C11 C4 -178.11(13)
C6 C7 C11 C4 -0.05(13)
C8 C7 C11 C13 -34.2(2)
C6 C7 C11 C13 143.82(12)
C8 C7 C11 C12 35.9(2)
C6 C7 C11 C12 -146.06(12)
C3 C4 C11 C7 177.18(13)
C5 C4 C11 C7 -0.60(13)
C3 C4 C11 C13 33.6(2)
C5 C4 C11 C13 -144.19(12)
C3 C4 C11 C12 -37.1(2)
C5 C4 C11 C12 145.08(12)
C7 C11 C12 C13 -109.80(14)
C4 C11 C12 C13 110.22(15)
C7 C11 C13 C12 110.78(14)
C4 C11 C13 C12 -111.49(14)
C4 C5 N1 C1 -0.73(18)
C6 C5 N1 C1 176.93(12)
C2 C1 N1 C5 -0.15(19)
C7 C6 N2 C10 -0.43(18)
C5 C6 N2 C10 -178.62(12)
C9 C10 N2 C6 -0.02(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659817
