#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:14:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178712 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/23/4082342.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_4082342
loop_
_publ_author_name
'Duke, Charles B.'
'Letterman, Roger G.'
'Johnson, Jermaine O.'
'Barr, James W.'
'Hu, Songnan'
'Ross, Charles R.'
'Webster, Charles Edwin'
'Burkey, Theodore J.'
_publ_section_title
;
 Photochemistry of Chromium Arene Tricarbonyl Complexes with Tethered
 Pyridinyl and Propenyl Groups: Investigations of the Effect of Ring Size
 on Chelate Formation, Structure, and Linkage Isomerization
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              485
_journal_paper_doi               10.1021/om400928k
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C18 H15 Cr N O3'
_chemical_formula_weight         345.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.457(2)
_cell_angle_beta                 110.8450(10)
_cell_angle_gamma                106.6500(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9515(3)
_cell_length_b                   10.2396(4)
_cell_length_c                   11.0854(4)
_cell_measurement_temperature    173(2)
_cell_volume                     791.70(5)
_computing_cell_refinement       'SMART, Bruker (2000)'
_computing_data_collection       'SMART, Bruker (2000)'
_computing_data_reduction        'XPREP, Bruker (2000)'
_computing_molecular_graphics    'Raster3D (Merritt, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXs-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  'osmic mirrors'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16621
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         69.51
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    6.066
_exptl_absorpt_correction_T_max  0.7123
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocky
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0272
_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)+(0.0506P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2712
_reflns_number_total             2857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400928k_si_002.cif
_cod_data_source_block           crpycc5
_cod_original_cell_volume        791.69(5)
_cod_database_code               4082342
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cr Cr 0.21871(3) 0.57198(2) 0.76085(2) 0.01796(11) Uani 1 1 d .
O1 O -0.17931(16) 0.58121(12) 0.64630(13) 0.0291(3) Uani 1 1 d .
C1O C -0.0267(2) 0.57659(16) 0.69037(17) 0.0221(3) Uani 1 1 d .
O2 O 0.07430(18) 0.28155(12) 0.60557(13) 0.0303(3) Uani 1 1 d .
C2O C 0.1317(2) 0.39393(17) 0.66445(17) 0.0230(3) Uani 1 1 d .
O3 O 0.12707(19) 0.43511(14) 0.97018(13) 0.0333(3) Uani 1 1 d .
C3O C 0.1634(2) 0.49035(17) 0.89151(17) 0.0239(4) Uani 1 1 d .
C1 C 0.3148(2) 0.79913(15) 0.75820(16) 0.0192(3) Uani 1 1 d .
C2 C 0.4106(2) 0.78078(16) 0.88552(16) 0.0204(3) Uani 1 1 d .
H2 H 0.4061 0.8303 0.9576 0.024 Uiso 1 1 calc R
C3 C 0.5143(2) 0.68700(17) 0.90477(17) 0.0228(3) Uani 1 1 d .
H3 H 0.5758 0.6745 0.9895 0.027 Uiso 1 1 calc R
C4 C 0.5255(2) 0.61307(17) 0.79830(17) 0.0240(4) Uani 1 1 d .
H4 H 0.5961 0.5532 0.8118 0.029 Uiso 1 1 calc R
C5 C 0.4283(2) 0.63031(16) 0.67008(17) 0.0226(3) Uani 1 1 d .
H5 H 0.4324 0.5799 0.5983 0.027 Uiso 1 1 calc R
C6 C 0.3255(2) 0.72284(16) 0.64974(17) 0.0206(3) Uani 1 1 d .
H6 H 0.2637 0.7345 0.5648 0.025 Uiso 1 1 calc R
C7 C 0.2012(2) 0.89895(16) 0.73101(16) 0.0196(3) Uani 1 1 d .
H7 H 0.0826 0.8524 0.6532 0.023 Uiso 1 1 calc R
C8 C 0.3170(2) 1.02647(16) 0.69693(16) 0.0197(3) Uani 1 1 d .
C9 C 0.2758(2) 1.04012(17) 0.56695(17) 0.0241(4) Uani 1 1 d .
H9 H 0.1751 0.9722 0.4987 0.029 Uiso 1 1 calc R
C10 C 0.3863(3) 1.15609(18) 0.54004(18) 0.0293(4) Uani 1 1 d .
H10 H 0.3610 1.1674 0.4536 0.035 Uiso 1 1 calc R
C11 C 0.5345(3) 1.25454(17) 0.64359(19) 0.0290(4) Uani 1 1 d .
H11 H 0.6115 1.3335 0.6287 0.035 Uiso 1 1 calc R
C12 C 0.5659(2) 1.23307(17) 0.76983(18) 0.0266(4) Uani 1 1 d .
H12 H 0.6659 1.2998 0.8394 0.032 Uiso 1 1 calc R
N N 0.4605(2) 1.12137(14) 0.79820(14) 0.0232(3) Uani 1 1 d .
C13 C 0.1468(2) 0.93831(17) 0.84545(17) 0.0224(3) Uani 1 1 d .
H13A H 0.0812 0.8541 0.8675 0.027 Uiso 1 1 calc R
H13B H 0.2622 0.9892 0.9223 0.027 Uiso 1 1 calc R
C14 C 0.0205(3) 1.02551(18) 0.81154(18) 0.0270(4) Uani 1 1 d .
H14 H 0.0651 1.1081 0.7853 0.032 Uiso 1 1 calc R
C15 C -0.1488(3) 0.9935(2) 0.8163(2) 0.0376(5) Uani 1 1 d .
H15A H -0.1978 0.9117 0.8421 0.045 Uiso 1 1 calc R
H15B H -0.2197 1.0525 0.7939 0.045 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr -0.1635 2.4439 '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_publ_flag
C2O Cr C1O 89.19(7) ?
C2O Cr C3O 86.46(7) ?
C1O Cr C3O 89.11(7) ?
C2O Cr C5 88.37(7) ?
C1O Cr C5 124.86(7) ?
C3O Cr C5 145.56(7) ?
C2O Cr C3 126.13(7) ?
C1O Cr C3 144.52(7) ?
C3O Cr C3 89.81(7) ?
C5 Cr C3 66.29(6) ?
C2O Cr C6 109.52(7) ?
C1O Cr C6 94.08(7) ?
C3O Cr C6 163.71(7) ?
C5 Cr C6 36.95(6) ?
C3 Cr C6 78.34(6) ?
C2O Cr C4 95.83(7) ?
C1O Cr C4 160.62(7) ?
C3O Cr C4 109.83(7) ?
C5 Cr C4 37.05(6) ?
C3 Cr C4 36.61(6) ?
C6 Cr C4 66.59(6) ?
C2O Cr C2 162.29(7) ?
C1O Cr C2 108.04(6) ?
C3O Cr C2 97.56(7) ?
C5 Cr C2 78.55(6) ?
C3 Cr C2 37.16(6) ?
C6 Cr C2 66.27(6) ?
C4 Cr C2 66.55(6) ?
C2O Cr C1 145.74(7) ?
C1O Cr C1 86.32(6) ?
C3O Cr C1 127.34(7) ?
C5 Cr C1 67.03(6) ?
C3 Cr C1 66.59(6) ?
C6 Cr C1 37.29(6) ?
C4 Cr C1 78.99(6) ?
C2 Cr C1 36.57(6) ?
O1 C1O Cr 179.14(14) ?
O2 C2O Cr 178.37(15) ?
O3 C3O Cr 177.66(15) ?
C2 C1 C6 118.71(14) ?
C2 C1 C7 122.74(14) ?
C6 C1 C7 118.55(14) ?
C2 C1 Cr 71.52(9) ?
C6 C1 Cr 70.58(9) ?
C7 C1 Cr 130.14(10) y
C1 C2 C3 120.22(15) ?
C1 C2 Cr 71.91(9) ?
C3 C2 Cr 70.82(9) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
Cr C2 H2 129.9 ?
C4 C3 C2 120.89(15) ?
C4 C3 Cr 72.16(9) ?
C2 C3 Cr 72.02(9) ?
C4 C3 H3 119.6 ?
C2 C3 H3 119.6 ?
Cr C3 H3 128.6 ?
C3 C4 C5 119.11(15) ?
C3 C4 Cr 71.24(9) ?
C5 C4 Cr 70.60(9) ?
C3 C4 H4 120.4 ?
C5 C4 H4 120.4 ?
Cr C4 H4 130.2 ?
C6 C5 C4 120.54(15) ?
C6 C5 Cr 71.96(9) ?
C4 C5 Cr 72.35(10) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
Cr C5 H5 128.2 ?
C5 C6 C1 120.50(15) ?
C5 C6 Cr 71.09(9) ?
C1 C6 Cr 72.13(9) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
Cr C6 H6 129.5 ?
C8 C7 C1 108.06(12) ?
C8 C7 C13 112.16(13) y
C1 C7 C13 113.07(13) y
C8 C7 H7 107.8 ?
C1 C7 H7 107.8 ?
C13 C7 H7 107.8 ?
N C8 C9 122.51(15) ?
N C8 C7 116.53(14) y
C9 C8 C7 120.94(14) ?
C10 C9 C8 119.19(16) ?
C10 C9 H9 120.4 ?
C8 C9 H9 120.4 ?
C11 C10 C9 118.81(16) ?
C11 C10 H10 120.6 ?
C9 C10 H10 120.6 ?
C10 C11 C12 118.35(16) ?
C10 C11 H11 120.8 ?
C12 C11 H11 120.8 ?
N C12 C11 123.84(16) ?
N C12 H12 118.1 ?
C11 C12 H12 118.1 ?
C8 N C12 117.30(15) ?
C14 C13 C7 111.99(14) y
C14 C13 H13A 109.2 ?
C7 C13 H13A 109.2 ?
C14 C13 H13B 109.2 ?
C7 C13 H13B 109.2 ?
H13A C13 H13B 107.9 ?
C15 C14 C13 124.52(17) y
C15 C14 H14 117.7 ?
C13 C14 H14 117.7 ?
C14 C15 H15A 120.0 ?
C14 C15 H15B 120.0 ?
H15A C15 H15B 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cr C2O 1.8420(17) y
Cr C1O 1.8426(17) y
Cr C3O 1.8495(19) y
Cr C5 2.2052(17) y
Cr C3 2.2160(16) y
Cr C6 2.2164(16) y
Cr C4 2.2278(16) y
Cr C2 2.2316(15) y
Cr C1 2.2367(15) y
O1 C1O 1.152(2) y
O2 C2O 1.153(2) y
O3 C3O 1.152(2) y
C1 C2 1.402(2) ?
C1 C6 1.424(2) ?
C1 C7 1.528(2) ?
C2 C3 1.417(2) ?
C2 H2 0.9300 ?
C3 C4 1.396(2) ?
C3 H3 0.9300 ?
C4 C5 1.408(2) ?
C4 H4 0.9300 ?
C5 C6 1.401(2) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.527(2) ?
C7 C13 1.540(2) ?
C7 H7 0.9800 ?
C8 N 1.338(2) ?
C8 C9 1.387(2) ?
C9 C10 1.384(2) ?
C9 H9 0.9300 ?
C10 C11 1.378(3) ?
C10 H10 0.9300 ?
C11 C12 1.378(3) ?
C11 H11 0.9300 ?
C12 N 1.343(2) ?
C12 H12 0.9300 ?
C13 C14 1.498(2) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 C15 1.312(3) y
C14 H14 0.9300 ?
C15 H15A 0.9300 ?
C15 H15B 0.9300 ?
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
_geom_torsion_publ_flag
C2O Cr C1 C2 -149.45(12) ?
C1O Cr C1 C2 127.42(10) ?
C3O Cr C1 C2 41.36(12) ?
C5 Cr C1 C2 -102.09(10) ?
C3 Cr C1 C2 -29.08(9) ?
C6 Cr C1 C2 -130.92(14) ?
C4 Cr C1 C2 -65.28(10) ?
C2O Cr C1 C6 -18.53(16) ?
C1O Cr C1 C6 -101.67(10) ?
C3O Cr C1 C6 172.27(10) ?
C5 Cr C1 C6 28.83(9) ?
C3 Cr C1 C6 101.83(10) ?
C4 Cr C1 C6 65.63(10) ?
C2 Cr C1 C6 130.92(14) ?
C2O Cr C1 C7 92.91(17) ?
C1O Cr C1 C7 9.77(15) ?
C3O Cr C1 C7 -76.28(16) ?
C5 Cr C1 C7 140.27(16) ?
C3 Cr C1 C7 -146.73(16) ?
C6 Cr C1 C7 111.44(18) ?
C4 Cr C1 C7 177.07(15) ?
C2 Cr C1 C7 -117.64(18) ?
C6 C1 C2 C3 -0.5(2) ?
C7 C1 C2 C3 -179.79(14) ?
Cr C1 C2 C3 53.82(13) ?
C6 C1 C2 Cr -54.35(13) ?
C7 C1 C2 Cr 126.39(14) ?
C2O Cr C2 C1 109.8(2) ?
C1O Cr C2 C1 -56.47(11) ?
C3O Cr C2 C1 -148.00(10) ?
C5 Cr C2 C1 66.72(10) ?
C3 Cr C2 C1 132.40(14) ?
C6 Cr C2 C1 30.01(9) ?
C4 Cr C2 C1 103.61(10) ?
C2O Cr C2 C3 -22.6(3) ?
C1O Cr C2 C3 171.13(10) ?
C3O Cr C2 C3 79.60(11) ?
C5 Cr C2 C3 -65.68(10) ?
C6 Cr C2 C3 -102.39(11) ?
C4 Cr C2 C3 -28.79(10) ?
C1 Cr C2 C3 -132.40(14) ?
C1 C2 C3 C4 0.9(2) ?
Cr C2 C3 C4 55.28(14) ?
C1 C2 C3 Cr -54.33(13) ?
C2O Cr C3 C4 39.50(13) ?
C1O Cr C3 C4 -146.81(12) ?
C3O Cr C3 C4 124.99(10) ?
C5 Cr C3 C4 -29.46(9) ?
C6 Cr C3 C4 -66.27(10) ?
C2 Cr C3 C4 -132.19(15) ?
C1 Cr C3 C4 -103.53(11) ?
C2O Cr C3 C2 171.69(10) ?
C1O Cr C3 C2 -14.63(17) ?
C3O Cr C3 C2 -102.83(10) ?
C5 Cr C3 C2 102.73(11) ?
C6 Cr C3 C2 65.92(10) ?
C4 Cr C3 C2 132.19(15) ?
C1 Cr C3 C2 28.65(9) ?
C2 C3 C4 C5 -1.4(2) ?
Cr C3 C4 C5 53.80(14) ?
C2 C3 C4 Cr -55.22(14) ?
C2O Cr C4 C3 -148.90(10) ?
C1O Cr C4 C3 106.8(2) ?
C3O Cr C4 C3 -60.57(11) ?
C5 Cr C4 C3 131.63(14) ?
C6 Cr C4 C3 102.33(11) ?
C2 Cr C4 C3 29.20(10) ?
C1 Cr C4 C3 65.35(10) ?
C2O Cr C4 C5 79.47(10) ?
C1O Cr C4 C5 -24.9(2) ?
C3O Cr C4 C5 167.80(10) ?
C3 Cr C4 C5 -131.63(14) ?
C6 Cr C4 C5 -29.31(9) ?
C2 Cr C4 C5 -102.43(10) ?
C1 Cr C4 C5 -66.28(10) ?
C3 C4 C5 C6 1.5(2) ?
Cr C4 C5 C6 55.59(13) ?
C3 C4 C5 Cr -54.10(14) ?
C2O Cr C5 C6 126.44(10) ?
C1O Cr C5 C6 38.56(12) ?
C3O Cr C5 C6 -152.22(12) ?
C3 Cr C5 C6 -102.51(10) ?
C4 Cr C5 C6 -131.64(14) ?
C2 Cr C5 C6 -65.56(10) ?
C1 Cr C5 C6 -29.08(9) ?
C2O Cr C5 C4 -101.92(10) ?
C1O Cr C5 C4 170.20(9) ?
C3O Cr C5 C4 -20.58(16) ?
C3 Cr C5 C4 29.13(9) ?
C6 Cr C5 C4 131.64(14) ?
C2 Cr C5 C4 66.08(10) ?
C1 Cr C5 C4 102.56(10) ?
C4 C5 C6 C1 -1.1(2) ?
Cr C5 C6 C1 54.67(13) ?
C4 C5 C6 Cr -55.78(14) ?
C2 C1 C6 C5 0.6(2) ?
C7 C1 C6 C5 179.90(14) ?
Cr C1 C6 C5 -54.19(13) ?
C2 C1 C6 Cr 54.80(13) ?
C7 C1 C6 Cr -125.90(13) ?
C2O Cr C6 C5 -58.56(11) ?
C1O Cr C6 C5 -149.15(10) ?
C3O Cr C6 C5 110.0(2) ?
C3 Cr C6 C5 65.88(10) ?
C4 Cr C6 C5 29.38(10) ?
C2 Cr C6 C5 102.92(11) ?
C1 Cr C6 C5 132.39(14) ?
C2O Cr C6 C1 169.06(9) ?
C1O Cr C6 C1 78.46(10) ?
C3O Cr C6 C1 -22.4(3) ?
C5 Cr C6 C1 -132.39(14) ?
C3 Cr C6 C1 -66.50(10) ?
C4 Cr C6 C1 -103.01(10) ?
C2 Cr C6 C1 -29.46(9) ?
C2 C1 C7 C8 105.67(17) y
C6 C1 C7 C8 -73.59(17) ?
Cr C1 C7 C8 -161.51(12) y
C2 C1 C7 C13 -19.1(2) y
C6 C1 C7 C13 161.66(14) ?
Cr C1 C7 C13 73.74(17) y
C1 C7 C8 N -79.23(17) y
C13 C7 C8 N 46.06(18) ?
C1 C7 C8 C9 99.56(17) ?
C13 C7 C8 C9 -135.15(15) ?
N C8 C9 C10 -0.1(2) ?
C7 C8 C9 C10 -178.85(15) ?
C8 C9 C10 C11 0.1(3) ?
C9 C10 C11 C12 -0.1(3) ?
C10 C11 C12 N 0.1(3) ?
C9 C8 N C12 0.1(2) ?
C7 C8 N C12 178.90(14) ?
C11 C12 N C8 -0.1(3) ?
C8 C7 C13 C14 62.76(18) ?
C1 C7 C13 C14 -174.75(13) y
C7 C13 C14 C15 123.41(19) y
