#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:14:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178712 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/23/4082336.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_4082336
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            'C15 H11 Cr N O3'
_chemical_formula_weight         305.25
_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                101.417(2)
_cell_angle_beta                 96.374(2)
_cell_angle_gamma                116.3470(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0221(3)
_cell_length_b                   8.1586(3)
_cell_length_c                   11.6167(6)
_cell_measurement_temperature    173(2)
_cell_volume                     650.50(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 0.967
_diffrn_measured_fraction_theta_max 0.954
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12995
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         69.17
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    7.299
_exptl_absorpt_correction_T_max  0.7117
_exptl_absorpt_correction_T_min  0.5007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.3128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                2259
_reflns_number_total             2315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400928k_si_002.cif
_cod_data_source_block           crpy5
_cod_database_code               4082336
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
Cr1 Cr 0.71866(4) 0.66497(4) 0.85759(2) 0.01223(12) Uani 1 1 d .
O3 O 0.8120(2) 0.7904(2) 1.12736(12) 0.0247(3) Uani 1 1 d .
O1 O 1.1348(2) 0.7942(2) 0.86810(15) 0.0328(4) Uani 1 1 d .
O2 O 0.6756(2) 0.2894(2) 0.88133(13) 0.0313(4) Uani 1 1 d .
C1 C 0.7100(2) 0.7808(3) 0.69840(16) 0.0141(4) Uani 1 1 d .
C5 C 0.5552(3) 0.8235(3) 0.86332(16) 0.0167(4) Uani 1 1 d .
H5 H 0.5481 0.9028 0.9299 0.020 Uiso 1 1 calc R
C3 C 0.4387(3) 0.5079(3) 0.72893(16) 0.0162(4) Uani 1 1 d .
H3 H 0.3555 0.3777 0.7066 0.019 Uiso 1 1 calc R
C8 C 0.8194(2) 0.9983(3) 0.56714(16) 0.0147(4) Uani 1 1 d .
C2 C 0.5797(3) 0.5843(3) 0.66350(16) 0.0151(4) Uani 1 1 d .
H2 H 0.5866 0.5045 0.5971 0.018 Uiso 1 1 calc R
C6 C 0.6969(3) 0.9000(3) 0.79961(16) 0.0146(4) Uani 1 1 d .
H6 H 0.7826 1.0296 0.8240 0.017 Uiso 1 1 calc R
C7 C 0.8603(3) 0.8678(3) 0.62838(16) 0.0166(4) Uani 1 1 d .
H7A H 0.9854 0.9397 0.6829 0.020 Uiso 1 1 calc R
H7B H 0.8611 0.7674 0.5681 0.020 Uiso 1 1 calc R
C4 C 0.4234(3) 0.6273(3) 0.82717(17) 0.0168(4) Uani 1 1 d .
H4 H 0.3273 0.5776 0.8681 0.020 Uiso 1 1 calc R
N1 N 0.7032(2) 0.9165(2) 0.45689(14) 0.0185(3) Uani 1 1 d .
C9 C 0.8972(3) 1.1918(3) 0.62437(16) 0.0175(4) Uani 1 1 d .
H9 H 0.9770 1.2443 0.7010 0.021 Uiso 1 1 calc R
C15 C 0.7763(3) 0.7437(3) 1.02312(17) 0.0172(4) Uani 1 1 d .
C10 C 0.8542(3) 1.3050(3) 0.56580(18) 0.0205(4) Uani 1 1 d .
H10 H 0.9041 1.4344 0.6024 0.025 Uiso 1 1 calc R
C11 C 0.7356(3) 1.2222(3) 0.45189(18) 0.0218(4) Uani 1 1 d .
H11 H 0.7049 1.2947 0.4100 0.026 Uiso 1 1 calc R
C13 C 0.9749(3) 0.7453(3) 0.86357(17) 0.0215(4) Uani 1 1 d .
C12 C 0.6632(3) 1.0283(3) 0.40142(17) 0.0210(4) Uani 1 1 d .
H12 H 0.5827 0.9729 0.3250 0.025 Uiso 1 1 calc R
C14 C 0.6919(3) 0.4332(3) 0.87014(16) 0.0200(4) 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 0.0181 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'
Cr Cr -0.1635 2.4439 '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'
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
C15 Cr1 C14 87.37(8) y
C15 Cr1 C13 88.57(8) y
C14 Cr1 C13 88.45(9) y
C15 Cr1 C3 129.91(8) ?
C14 Cr1 C3 87.76(8) ?
C13 Cr1 C3 141.05(8) ?
C15 Cr1 C5 86.67(7) ?
C14 Cr1 C5 139.96(8) ?
C13 Cr1 C5 130.89(8) ?
C3 Cr1 C5 66.66(7) ?
C15 Cr1 C6 105.05(7) ?
C14 Cr1 C6 165.64(8) ?
C13 Cr1 C6 98.86(8) ?
C3 Cr1 C6 78.77(7) ?
C5 Cr1 C6 36.90(7) ?
C15 Cr1 C4 97.71(8) ?
C14 Cr1 C4 105.13(8) ?
C13 Cr1 C4 165.21(8) ?
C3 Cr1 C4 36.85(7) ?
C5 Cr1 C4 37.07(7) ?
C6 Cr1 C4 66.63(7) ?
C15 Cr1 C2 163.84(8) ?
C14 Cr1 C2 99.86(7) ?
C13 Cr1 C2 105.93(8) ?
C3 Cr1 C2 37.20(7) ?
C5 Cr1 C2 78.49(7) ?
C6 Cr1 C2 66.31(7) ?
C4 Cr1 C2 66.53(7) ?
C15 Cr1 C1 140.25(8) ?
C14 Cr1 C1 132.05(7) ?
C13 Cr1 C1 87.85(8) ?
C3 Cr1 C1 66.81(7) ?
C5 Cr1 C1 66.60(6) ?
C6 Cr1 C1 36.96(7) ?
C4 Cr1 C1 78.75(7) ?
C2 Cr1 C1 36.75(7) ?
C2 C1 C6 118.94(16) ?
C2 C1 C7 121.65(16) y
C6 C1 C7 119.39(16) ?
C2 C1 Cr1 70.97(10) ?
C6 C1 Cr1 70.70(10) ?
C7 C1 Cr1 131.57(12) y
C6 C5 C4 120.55(16) ?
C6 C5 Cr1 72.03(10) ?
C4 C5 Cr1 72.05(10) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
Cr1 C5 H5 128.5 ?
C4 C3 C2 120.41(17) ?
C4 C3 Cr1 72.38(10) ?
C2 C3 Cr1 72.26(10) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
Cr1 C3 H3 127.7 ?
N1 C8 C9 122.47(17) ?
N1 C8 C7 116.39(16) y
C9 C8 C7 121.14(16) ?
C1 C2 C3 120.37(16) ?
C1 C2 Cr1 72.28(10) ?
C3 C2 Cr1 70.54(10) ?
C1 C2 H2 119.8 ?
C3 C2 H2 119.8 ?
Cr1 C2 H2 129.9 ?
C5 C6 C1 120.36(17) ?
C5 C6 Cr1 71.07(10) ?
C1 C6 Cr1 72.34(10) ?
C5 C6 H6 119.8 ?
C1 C6 H6 119.8 ?
Cr1 C6 H6 129.1 ?
C8 C7 C1 110.58(14) y
C8 C7 H7A 109.5 ?
C1 C7 H7A 109.5 ?
C8 C7 H7B 109.5 ?
C1 C7 H7B 109.5 ?
H7A C7 H7B 108.1 ?
C3 C4 C5 119.32(16) ?
C3 C4 Cr1 70.77(10) ?
C5 C4 Cr1 70.88(10) ?
C3 C4 H4 120.3 ?
C5 C4 H4 120.3 ?
Cr1 C4 H4 130.6 ?
C12 N1 C8 117.56(16) ?
C10 C9 C8 119.18(17) ?
C10 C9 H9 120.4 ?
C8 C9 H9 120.4 ?
O3 C15 Cr1 178.92(16) ?
C11 C10 C9 118.73(18) ?
C11 C10 H10 120.6 ?
C9 C10 H10 120.6 ?
C10 C11 C12 118.52(18) ?
C10 C11 H11 120.7 ?
C12 C11 H11 120.7 ?
O1 C13 Cr1 179.28(18) ?
N1 C12 C11 123.54(18) ?
N1 C12 H12 118.2 ?
C11 C12 H12 118.2 ?
O2 C14 Cr1 178.17(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cr1 C15 1.8369(19) y
Cr1 C14 1.843(2) y
Cr1 C13 1.848(2) y
Cr1 C3 2.2052(18) y
Cr1 C5 2.2108(18) y
Cr1 C6 2.2231(18) y
Cr1 C4 2.2259(18) y
Cr1 C2 2.2276(18) y
Cr1 C1 2.2445(17) y
O3 C15 1.156(2) y
O1 C13 1.153(3) y
O2 C14 1.158(3) y
C1 C2 1.410(3) ?
C1 C6 1.416(3) ?
C1 C7 1.519(2) ?
C5 C6 1.403(3) ?
C5 C4 1.410(3) ?
C5 H5 0.9300 ?
C3 C4 1.401(3) ?
C3 C2 1.414(3) ?
C3 H3 0.9300 ?
C8 N1 1.341(2) ?
C8 C9 1.393(3) ?
C8 C7 1.518(2) ?
C2 H2 0.9300 ?
C6 H6 0.9300 ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C4 H4 0.9300 ?
N1 C12 1.340(3) ?
C9 C10 1.384(3) ?
C9 H9 0.9300 ?
C10 C11 1.382(3) ?
C10 H10 0.9300 ?
C11 C12 1.387(3) ?
C11 H11 0.9300 ?
C12 H12 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
C15 Cr1 C1 C2 -154.20(12) ?
C14 Cr1 C1 C2 34.66(14) ?
C13 Cr1 C1 C2 120.63(12) ?
C3 Cr1 C1 C2 -29.00(10) ?
C5 Cr1 C1 C2 -102.48(11) ?
C6 Cr1 C1 C2 -131.54(15) ?
C4 Cr1 C1 C2 -65.65(11) ?
C15 Cr1 C1 C6 -22.66(16) ?
C14 Cr1 C1 C6 166.21(12) ?
C13 Cr1 C1 C6 -107.83(12) ?
C3 Cr1 C1 C6 102.54(11) ?
C5 Cr1 C1 C6 29.06(10) ?
C4 Cr1 C1 C6 65.90(11) ?
C2 Cr1 C1 C6 131.54(15) ?
C15 Cr1 C1 C7 90.0(2) ?
C14 Cr1 C1 C7 -81.2(2) ?
C13 Cr1 C1 C7 4.78(18) ?
C3 Cr1 C1 C7 -144.84(19) ?
C5 Cr1 C1 C7 141.67(19) ?
C6 Cr1 C1 C7 112.6(2) ?
C4 Cr1 C1 C7 178.51(18) ?
C2 Cr1 C1 C7 -115.8(2) ?
C15 Cr1 C5 C6 120.72(12) ?
C14 Cr1 C5 C6 -157.38(12) ?
C13 Cr1 C5 C6 35.50(15) ?
C3 Cr1 C5 C6 -102.81(12) ?
C4 Cr1 C5 C6 -131.82(16) ?
C2 Cr1 C5 C6 -65.70(11) ?
C1 Cr1 C5 C6 -29.10(10) ?
C15 Cr1 C5 C4 -107.46(11) ?
C14 Cr1 C5 C4 -25.56(16) ?
C13 Cr1 C5 C4 167.32(11) ?
C3 Cr1 C5 C4 29.01(10) ?
C6 Cr1 C5 C4 131.82(16) ?
C2 Cr1 C5 C4 66.12(11) ?
C1 Cr1 C5 C4 102.72(11) ?
C15 Cr1 C3 C4 34.50(15) ?
C14 Cr1 C3 C4 119.19(12) ?
C13 Cr1 C3 C4 -156.06(13) ?
C5 Cr1 C3 C4 -29.17(10) ?
C6 Cr1 C3 C4 -65.82(11) ?
C2 Cr1 C3 C4 -131.24(16) ?
C1 Cr1 C3 C4 -102.57(12) ?
C15 Cr1 C3 C2 165.74(11) ?
C14 Cr1 C3 C2 -109.57(12) ?
C13 Cr1 C3 C2 -24.82(17) ?
C5 Cr1 C3 C2 102.07(11) ?
C6 Cr1 C3 C2 65.42(11) ?
C4 Cr1 C3 C2 131.24(16) ?
C1 Cr1 C3 C2 28.67(10) ?
C6 C1 C2 C3 -0.2(3) ?
C7 C1 C2 C3 -178.61(16) ?
Cr1 C1 C2 C3 53.66(15) ?
C6 C1 C2 Cr1 -53.83(14) ?
C7 C1 C2 Cr1 127.73(16) ?
C4 C3 C2 C1 1.7(3) ?
Cr1 C3 C2 C1 -54.47(15) ?
C4 C3 C2 Cr1 56.20(15) ?
C15 Cr1 C2 C1 89.8(3) ?
C14 Cr1 C2 C1 -154.62(11) ?
C13 Cr1 C2 C1 -63.41(12) ?
C3 Cr1 C2 C1 132.51(15) ?
C5 Cr1 C2 C1 66.13(11) ?
C6 Cr1 C2 C1 29.43(10) ?
C4 Cr1 C2 C1 103.06(11) ?
C15 Cr1 C2 C3 -42.8(3) ?
C14 Cr1 C2 C3 72.87(12) ?
C13 Cr1 C2 C3 164.07(11) ?
C5 Cr1 C2 C3 -66.39(11) ?
C6 Cr1 C2 C3 -103.08(11) ?
C4 Cr1 C2 C3 -29.45(11) ?
C1 Cr1 C2 C3 -132.51(15) ?
C4 C5 C6 C1 -0.3(3) ?
Cr1 C5 C6 C1 55.08(15) ?
C4 C5 C6 Cr1 -55.41(15) ?
C2 C1 C6 C5 -0.5(3) ?
C7 C1 C6 C5 177.95(16) ?
Cr1 C1 C6 C5 -54.48(15) ?
C2 C1 C6 Cr1 53.96(14) ?
C7 C1 C6 Cr1 -127.57(15) ?
C15 Cr1 C6 C5 -62.71(12) ?
C14 Cr1 C6 C5 86.5(3) ?
C13 Cr1 C6 C5 -153.62(11) ?
C3 Cr1 C6 C5 65.89(11) ?
C4 Cr1 C6 C5 29.30(11) ?
C2 Cr1 C6 C5 102.79(12) ?
C1 Cr1 C6 C5 132.06(16) ?
C15 Cr1 C6 C1 165.22(11) ?
C14 Cr1 C6 C1 -45.6(3) ?
C13 Cr1 C6 C1 74.32(12) ?
C3 Cr1 C6 C1 -66.17(11) ?
C5 Cr1 C6 C1 -132.06(16) ?
C4 Cr1 C6 C1 -102.76(12) ?
C2 Cr1 C6 C1 -29.28(10) ?
N1 C8 C7 C1 -87.85(19) y
C9 C8 C7 C1 91.2(2) ?
C2 C1 C7 C8 112.67(19) y
C6 C1 C7 C8 -65.8(2) ?
Cr1 C1 C7 C8 -155.34(13) y
C2 C3 C4 C5 -2.6(3) ?
Cr1 C3 C4 C5 53.57(15) ?
C2 C3 C4 Cr1 -56.14(15) ?
C6 C5 C4 C3 1.9(3) ?
Cr1 C5 C4 C3 -53.52(15) ?
C6 C5 C4 Cr1 55.40(15) ?
C15 Cr1 C4 C3 -154.00(11) ?
C14 Cr1 C4 C3 -64.65(12) ?
C13 Cr1 C4 C3 91.5(3) ?
C5 Cr1 C4 C3 132.06(16) ?
C6 Cr1 C4 C3 102.89(12) ?
C2 Cr1 C4 C3 29.71(10) ?
C1 Cr1 C4 C3 66.17(11) ?
C15 Cr1 C4 C5 73.94(11) ?
C14 Cr1 C4 C5 163.29(11) ?
C13 Cr1 C4 C5 -40.6(3) ?
C3 Cr1 C4 C5 -132.06(16) ?
C6 Cr1 C4 C5 -29.17(10) ?
C2 Cr1 C4 C5 -102.35(11) ?
C1 Cr1 C4 C5 -65.89(11) ?
C9 C8 N1 C12 0.3(3) ?
C7 C8 N1 C12 179.31(16) ?
N1 C8 C9 C10 -0.2(3) ?
C7 C8 C9 C10 -179.18(16) ?
C8 C9 C10 C11 -0.2(3) ?
C9 C10 C11 C12 0.5(3) ?
C8 N1 C12 C11 0.1(3) ?
C10 C11 C12 N1 -0.5(3) ?
