#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/76/2227620.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_2227620
loop_
_publ_author_name
'van Tonder, Johannes H.'
'Bezuidenhoudt, Barend C. B.'
'Janse van Rensburg, J. Marthinus'
_publ_section_title
;
 Racemic
 tricarbonyl[(4a,5,6,7,8,8a-η)-2-phenyl-3,4-dihydro-2H-1-benzopyran]chromium(0)
;
_journal_coeditor_code           HY2329
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1086
_journal_paper_doi               10.1107/S1600536810031028
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cr (C15 H14 O) (C O)3]'
_chemical_formula_moiety         'C18 H14 Cr O4'
_chemical_formula_sum            'C18 H14 Cr O4'
_chemical_formula_weight         346.29
_chemical_name_common
;
Tricarbonyl(A-η⁶-flavan)chromium(0)
;
_chemical_name_systematic
;
tricarbonyl(η⁶-2-phenyl-1-benzopyran)chromium(0)
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.7170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0275(2)
_cell_length_b                   13.1454(2)
_cell_length_c                   10.4473(2)
_cell_measurement_reflns_used    4557
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      2.39
_cell_volume                     1534.54(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20468
_diffrn_reflns_theta_full        32.06
_diffrn_reflns_theta_max         32.06
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.9376
_exptl_absorpt_correction_T_min  0.7657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0469P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3728
_reflns_number_total             5342
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            hy2329.cif
_cod_data_source_block           I
_cod_original_cell_volume        1534.55(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227620
_cod_database_fobs_code          2227620
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1' 0.42382(14) 0.18308(12) 0.19968(17) 0.0245(3) Uani d . 1 . .
C C2 0.50936(14) 0.20966(13) 0.12917(17) 0.0263(3) Uani d . 1 . .
H H2 0.4643 0.2420 0.0405 0.032 Uiso calc R 1 . .
C C2' 0.32347(17) 0.24327(15) 0.1760(2) 0.0372(4) Uani d . 1 . .
H H2' 0.3095 0.2986 0.1167 0.045 Uiso calc R 1 . .
C C3 0.60863(15) 0.27990(13) 0.21249(18) 0.0293(4) Uani d . 1 . .
H H3A 0.6526 0.2491 0.3013 0.035 Uiso calc R 1 . .
H H3B 0.5746 0.3433 0.2285 0.035 Uiso calc R 1 . .
C C3' 0.24388(17) 0.22168(16) 0.2401(2) 0.0405(5) Uani d . 1 . .
H H3' 0.1772 0.2629 0.2240 0.049 Uiso calc R 1 . .
C C4 0.69396(15) 0.30169(12) 0.13848(18) 0.0269(3) Uani d . 1 . .
H H4A 0.6552 0.3457 0.0600 0.032 Uiso calc R 1 . .
H H4B 0.7645 0.3364 0.2005 0.032 Uiso calc R 1 . .
C C4' 0.26295(15) 0.13974(15) 0.32735(18) 0.0327(4) Uani d . 1 . .
H H4' 0.2084 0.1245 0.3686 0.039 Uiso calc R 1 . .
C C5' 0.36356(16) 0.08021(13) 0.35341(18) 0.0295(4) Uani d . 1 . .
H H5' 0.3773 0.0254 0.4135 0.035 Uiso calc R 1 . .
C C5 0.83325(14) 0.19620(13) 0.05541(16) 0.0261(3) Uani d . 1 . .
H H5 0.8817 0.2531 0.0654 0.031 Uiso calc R 1 . .
C C6' 0.44412(14) 0.10155(12) 0.29068(18) 0.0260(3) Uani d . 1 . .
H H6' 0.5119 0.0614 0.3094 0.031 Uiso calc R 1 . .
C C6 0.86366(15) 0.10536(13) 0.00632(17) 0.0290(4) Uani d . 1 . .
H H6 0.9293 0.1028 -0.0204 0.035 Uiso calc R 1 . .
C C7 0.79393(15) 0.01836(14) -0.00212(18) 0.0309(4) Uani d . 1 . .
H H7 0.8147 -0.0427 -0.0322 0.037 Uiso calc R 1 . .
C C8 0.69312(14) 0.02274(13) 0.03445(17) 0.0278(4) Uani d . 1 . .
H H8 0.6488 -0.0357 0.0319 0.033 Uiso calc R 1 . .
C C9 0.65942(13) 0.11637(12) 0.07510(16) 0.0223(3) Uani d . 1 . .
C C10 0.72998(13) 0.20345(12) 0.09035(15) 0.0219(3) Uani d . 1 . .
C C11 0.79274(15) 0.03598(13) 0.34020(18) 0.0297(4) Uani d . 1 . .
C C12 0.96333(16) -0.02379(14) 0.26452(19) 0.0334(4) Uani d . 1 . .
C C13 0.95879(14) 0.16059(13) 0.34028(17) 0.0267(3) Uani d . 1 . .
O O1 0.75227(13) 0.00961(11) 0.41970(15) 0.0468(4) Uani d . 1 . .
O O2 1.03289(14) -0.08866(11) 0.29813(18) 0.0576(4) Uani d . 1 . .
O O3 1.02610(11) 0.21213(11) 0.42255(14) 0.0422(3) Uani d . 1 . .
O O5 0.55780(9) 0.11377(8) 0.10382(12) 0.0260(2) Uani d . 1 . .
Cr Cr 0.85184(2) 0.078021(19) 0.21024(3) 0.02026(7) Uani d . 1 . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2' C1' C6' . . 118.79(15) ?
C2' C1' C2 . . 119.07(15) ?
C6' C1' C2 . . 122.11(14) ?
O5 C2 C3 . . 110.59(13) ?
O5 C2 C1' . . 106.22(13) ?
C3 C2 C1' . . 113.41(14) ?
O5 C2 H2 . . 108.8 ?
C3 C2 H2 . . 108.8 ?
C1' C2 H2 . . 108.8 ?
C3' C2' C1' . . 120.57(17) ?
C3' C2' H2' . . 119.7 ?
C1' C2' H2' . . 119.7 ?
C2 C3 C4 . . 111.16(14) ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C4' C3' C2' . . 120.36(17) ?
C4' C3' H3' . . 119.8 ?
C2' C3' H3' . . 119.8 ?
C10 C4 C3 . . 109.83(13) ?
C10 C4 H4A . . 109.7 ?
C3 C4 H4A . . 109.7 ?
C10 C4 H4B . . 109.7 ?
C3 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
C3' C4' C5' . . 119.60(16) ?
C3' C4' H4' . . 120.2 ?
C5' C4' H4' . . 120.2 ?
C4' C5' C6' . . 120.51(16) ?
C4' C5' H5' . . 119.7 ?
C6' C5' H5' . . 119.7 ?
C6 C5 C10 . . 121.51(15) ?
C6 C5 Cr . . 72.37(10) ?
C10 C5 Cr . . 73.65(9) ?
C6 C5 H5 . . 119.2 ?
C10 C5 H5 . . 119.2 ?
Cr C5 H5 . . 126.7 ?
C5' C6' C1' . . 120.15(15) ?
C5' C6' H6' . . 119.9 ?
C1' C6' H6' . . 119.9 ?
C5 C6 C7 . . 119.17(15) ?
C5 C6 Cr . . 70.60(9) ?
C7 C6 Cr . . 71.24(9) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
Cr C6 H6 . . 130.2 ?
C8 C7 C6 . . 120.50(16) ?
C8 C7 Cr . . 72.22(10) ?
C6 C7 Cr . . 71.83(10) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
Cr C7 H7 . . 128.5 ?
C7 C8 C9 . . 119.50(15) ?
C7 C8 Cr . . 70.95(10) ?
C9 C8 Cr . . 73.78(9) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
Cr C8 H8 . . 127.0 ?
O5 C9 C10 . . 123.47(14) ?
O5 C9 C8 . . 115.20(14) ?
C10 C9 C8 . . 121.26(14) ?
O5 C9 Cr . . 130.29(11) ?
C10 C9 Cr . . 71.08(9) ?
C8 C9 Cr . . 69.75(9) ?
C9 C10 C5 . . 117.84(15) ?
C9 C10 C4 . . 120.15(13) ?
C5 C10 C4 . . 121.99(14) ?
C9 C10 Cr . . 72.96(9) ?
C5 C10 Cr . . 69.09(9) ?
C4 C10 Cr . . 130.54(11) ?
O1 C11 Cr . . 178.15(15) ?
O2 C12 Cr . . 179.38(19) ?
O3 C13 Cr . . 179.64(17) ?
C9 O5 C2 . . 118.10(12) ?
C12 Cr C11 . . 89.46(8) ?
C12 Cr C13 . . 88.32(8) ?
C11 Cr C13 . . 89.30(8) ?
C12 Cr C5 . . 127.56(7) ?
C11 Cr C5 . . 142.85(7) ?
C13 Cr C5 . . 88.82(8) ?
C12 Cr C7 . . 88.52(8) ?
C11 Cr C7 . . 124.86(8) ?
C13 Cr C7 . . 145.65(7) ?
C5 Cr C7 . . 66.58(7) ?
C12 Cr C6 . . 96.67(8) ?
C11 Cr C6 . . 160.06(7) ?
C13 Cr C6 . . 109.76(7) ?
C5 Cr C6 . . 37.03(6) ?
C7 Cr C6 . . 36.93(7) ?
C12 Cr C8 . . 108.88(8) ?
C11 Cr C8 . . 93.63(8) ?
C13 Cr C8 . . 162.56(7) ?
C5 Cr C8 . . 78.49(7) ?
C7 Cr C8 . . 36.83(6) ?
C6 Cr C8 . . 66.43(7) ?
C12 Cr C10 . . 163.51(7) ?
C11 Cr C10 . . 106.33(7) ?
C13 Cr C10 . . 96.43(7) ?
C5 Cr C10 . . 37.25(6) ?
C7 Cr C10 . . 78.64(7) ?
C6 Cr C10 . . 66.85(6) ?
C8 Cr C10 . . 66.24(6) ?
C12 Cr C9 . . 144.51(7) ?
C11 Cr C9 . . 86.69(7) ?
C13 Cr C9 . . 126.85(7) ?
C5 Cr C9 . . 65.36(6) ?
C7 Cr C9 . . 65.51(6) ?
C6 Cr C9 . . 77.30(6) ?
C8 Cr C9 . . 36.47(6) ?
C10 Cr C9 . . 35.96(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1' C2' . 1.387(2) ?
C1' C6' . 1.393(2) ?
C1' C2 . 1.511(2) ?
C2 O5 . 1.4535(19) ?
C2 C3 . 1.506(2) ?
C2 H2 . 0.9800 ?
C2' C3' . 1.385(3) ?
C2' H2' . 0.9300 ?
C3 C4 . 1.523(2) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C3' C4' . 1.374(3) ?
C3' H3' . 0.9300 ?
C4 C10 . 1.506(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C4' C5' . 1.381(2) ?
C4' H4' . 0.9300 ?
C5' C6' . 1.384(2) ?
C5' H5' . 0.9300 ?
C5 C6 . 1.401(2) ?
C5 C10 . 1.421(2) ?
C5 H5 . 0.9300 ?
C6' H6' . 0.9300 ?
C6 C7 . 1.401(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.401(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.410(2) ?
C8 H8 . 0.9300 ?
C9 O5 . 1.3627(18) ?
C9 C10 . 1.399(2) ?
C11 O1 . 1.160(2) ?
C12 O2 . 1.155(2) ?
C13 O3 . 1.157(2) ?
C5 Cr . 2.1936(18) y
C6 Cr . 2.2163(19) y
C7 Cr . 2.2087(19) y
C8 Cr . 2.2251(17) y
C9 Cr . 2.2773(17) y
C10 Cr . 2.2532(17) y
C11 Cr . 1.8353(19) y
C12 Cr . 1.8298(19) y
C13 Cr . 1.8399(17) y
