#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:38:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178957 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/86/4118635.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_4118635
loop_
_publ_author_name
'Deven P. Estes'
'Jack R. Norton'
'Steffen Jockusch'
'Wesley Sattler'
_publ_section_title
;
 Mechanisms by which Alkynes React with CpCr(CO)3H. Application to Radical
 Cyclization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15512
_journal_page_last               15518
_journal_paper_doi               10.1021/ja306120n
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C16 H12 Cr O3'
_chemical_formula_weight         304.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 112.791(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.281(4)
_cell_length_b                   11.029(4)
_cell_length_c                   12.894(4)
_cell_measurement_reflns_used    2839
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      2.83
_cell_volume                     1347.9(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.1823
_diffrn_reflns_av_sigmaI/netI    0.1648
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20776
_diffrn_reflns_theta_full        31.01
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.8348
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1868
_refine_ls_R_factor_gt           0.0636
_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)+(0.0626P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                1812
_reflns_number_total             4225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja306120n_si_002.cif
_cod_data_source_block           dews10
_cod_database_code               4118635
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cr1 Cr 0.01200(7) 0.07017(6) 0.23318(5) 0.0253(2) Uani 1 1 d .
C1 C 0.1408(4) -0.0156(4) 0.3881(3) 0.0318(10) Uani 1 1 d .
H1A H 0.2061 -0.0854 0.3962 0.038 Uiso 1 1 calc R
C2 C 0.1791(5) 0.1061(4) 0.4026(3) 0.0363(11) Uani 1 1 d .
H2A H 0.2753 0.1390 0.4177 0.044 Uiso 1 1 calc R
C3 C 0.0577(5) 0.1764(4) 0.3906(3) 0.0345(11) Uani 1 1 d .
H3A H 0.0543 0.2667 0.3960 0.041 Uiso 1 1 calc R
C4 C -0.0556(4) 0.0977(4) 0.3696(3) 0.0286(10) Uani 1 1 d .
H4A H -0.1528 0.1219 0.3616 0.034 Uiso 1 1 calc R
C5 C -0.0098(4) -0.0243(4) 0.3628(3) 0.0271(9) Uani 1 1 d .
C6 C -0.0966(4) -0.1094(4) 0.2848(3) 0.0263(9) Uani 1 1 d .
C7 C -0.2552(4) -0.1030(4) 0.2439(4) 0.0363(11) Uani 1 1 d .
H7A H -0.2878 -0.1589 0.2878 0.054 Uiso 1 1 calc R
H7B H -0.2973 -0.1258 0.1642 0.054 Uiso 1 1 calc R
H7C H -0.2835 -0.0202 0.2530 0.054 Uiso 1 1 calc R
C11 C -0.0406(4) -0.2290(4) 0.2692(3) 0.0278(10) Uani 1 1 d .
C12 C -0.0803(4) -0.2802(4) 0.1628(4) 0.0313(10) Uani 1 1 d .
H12A H -0.1433 -0.2379 0.0989 0.038 Uiso 1 1 calc R
C13 C -0.0286(4) -0.3922(4) 0.1493(4) 0.0342(11) Uani 1 1 d .
H13A H -0.0554 -0.4261 0.0762 0.041 Uiso 1 1 calc R
C14 C 0.0623(5) -0.4552(4) 0.2420(4) 0.0389(12) Uani 1 1 d .
H14A H 0.0988 -0.5317 0.2327 0.047 Uiso 1 1 calc R
C15 C 0.0991(5) -0.4066(4) 0.3471(4) 0.0385(12) Uani 1 1 d .
H15A H 0.1599 -0.4505 0.4109 0.046 Uiso 1 1 calc R
C16 C 0.0490(5) -0.2948(4) 0.3613(4) 0.0332(11) Uani 1 1 d .
H16A H 0.0758 -0.2621 0.4348 0.040 Uiso 1 1 calc R
C21 C 0.0716(5) 0.1948(4) 0.1657(4) 0.0357(11) Uani 1 1 d .
C31 C -0.1656(4) 0.0994(4) 0.1263(3) 0.0285(10) Uani 1 1 d .
C41 C 0.0767(4) -0.0351(4) 0.1508(4) 0.0288(10) Uani 1 1 d .
O21 O 0.1052(4) 0.2704(3) 0.1207(3) 0.0517(9) Uani 1 1 d .
O31 O -0.2785(3) 0.1185(3) 0.0622(2) 0.0416(8) Uani 1 1 d .
O41 O 0.1197(3) -0.0989(3) 0.1018(3) 0.0369(8) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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
C31 Cr1 C21 86.05(19)
C31 Cr1 C41 98.74(18)
C21 Cr1 C41 86.45(19)
C31 Cr1 C5 107.98(18)
C21 Cr1 C5 156.70(18)
C41 Cr1 C5 108.88(17)
C31 Cr1 C1 148.34(18)
C21 Cr1 C1 124.60(19)
C41 Cr1 C1 91.62(18)
C5 Cr1 C1 40.56(16)
C31 Cr1 C4 92.66(17)
C21 Cr1 C4 123.40(17)
C41 Cr1 C4 148.82(17)
C5 Cr1 C4 39.98(15)
C1 Cr1 C4 65.06(16)
C31 Cr1 C2 150.06(17)
C21 Cr1 C2 93.38(19)
C41 Cr1 C2 111.11(17)
C5 Cr1 C2 65.08(17)
C1 Cr1 C2 37.04(17)
C4 Cr1 C2 62.85(16)
C31 Cr1 C3 112.79(17)
C21 Cr1 C3 92.67(18)
C41 Cr1 C3 148.34(17)
C5 Cr1 C3 64.97(17)
C1 Cr1 C3 63.09(16)
C4 Cr1 C3 37.03(16)
C2 Cr1 C3 37.28(15)
C31 Cr1 C6 85.52(16)
C21 Cr1 C6 168.62(16)
C41 Cr1 C6 87.29(16)
C5 Cr1 C6 34.58(15)
C1 Cr1 C6 65.06(15)
C4 Cr1 C6 64.67(15)
C2 Cr1 C6 97.74(16)
C3 Cr1 C6 97.63(16)
C2 C1 C5 108.3(4)
C2 C1 Cr1 74.9(3)
C5 C1 Cr1 66.5(2)
C1 C2 C3 108.7(4)
C1 C2 Cr1 68.0(2)
C3 C2 Cr1 71.4(2)
C4 C3 C2 108.2(4)
C4 C3 Cr1 68.3(2)
C2 C3 Cr1 71.3(2)
C3 C4 C5 109.0(4)
C3 C4 Cr1 74.7(3)
C5 C4 Cr1 66.5(2)
C6 C5 C4 122.2(4)
C6 C5 C1 121.8(4)
C4 C5 C1 105.6(4)
C6 C5 Cr1 89.8(3)
C4 C5 Cr1 73.5(2)
C1 C5 Cr1 72.9(2)
C5 C6 C11 121.1(3)
C5 C6 C7 121.1(4)
C11 C6 C7 114.7(3)
C5 C6 Cr1 55.7(2)
C11 C6 Cr1 115.7(3)
C7 C6 Cr1 113.9(3)
C12 C11 C16 118.4(4)
C12 C11 C6 120.9(4)
C16 C11 C6 120.7(4)
C13 C12 C11 120.4(4)
C12 C13 C14 120.2(4)
C15 C14 C13 119.6(4)
C14 C15 C16 120.6(4)
C15 C16 C11 120.7(4)
O21 C21 Cr1 177.7(4)
O31 C31 Cr1 177.7(4)
O41 C41 Cr1 178.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cr1 C31 1.841(4)
Cr1 C21 1.854(5)
Cr1 C41 1.862(5)
Cr1 C5 2.055(4)
Cr1 C1 2.142(4)
Cr1 C4 2.149(4)
Cr1 C2 2.230(4)
Cr1 C3 2.231(4)
Cr1 C6 2.488(4)
C1 C2 1.391(6)
C1 C5 1.457(6)
C2 C3 1.426(6)
C3 C4 1.393(6)
C4 C5 1.440(6)
C5 C6 1.412(6)
C6 C11 1.484(6)
C6 C7 1.508(6)
C11 C12 1.391(6)
C11 C16 1.392(5)
C12 C13 1.382(6)
C13 C14 1.386(6)
C14 C15 1.366(6)
C15 C16 1.376(6)
C21 O21 1.143(5)
C31 O31 1.154(5)
C41 O41 1.142(5)
