#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/96/4069621.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_4069621
loop_
_publ_author_name
'Semproni, Scott P.'
'Graham, Peter M.'
'Buschhaus, Miriam S. A.'
'Patrick, Brian O.'
'Legzdins, Peter'
_publ_section_title
;
 Toward Alkane Functionalization Effected with Cp*W(NO)(alkyl)(η3-allyl)
 Complexes
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4480
_journal_paper_doi               10.1021/om900307p
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C23 H22'
_chemical_formula_sum            'C23 H22'
_chemical_formula_weight         298.41
_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                 93.563(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0109(10)
_cell_length_b                   14.4336(9)
_cell_length_c                   7.2497(4)
_cell_measurement_reflns_used    3628
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      1.9
_cell_volume                     1672.13(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.858
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_device_type  'Bruker x8 Apex II'
_diffrn_measurement_method       'Area Detector'
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9091
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.8757
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0404
_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)+(0.0398P)²+0.4646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                2352
_reflns_number_total             3260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900307p_si_001.cif
_cod_data_source_block           pl346a
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4069621
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 0.94614(12) 0.39701(14) 0.3798(2) 0.0504(5) Uani 1 1 d .
H1A H 0.9259 0.4549 0.3220 0.076 Uiso 1 1 calc R
H1B H 0.9382 0.3460 0.2911 0.076 Uiso 1 1 calc R
H1C H 1.0057 0.4030 0.4174 0.076 Uiso 1 1 calc R
C2 C 0.89823(11) 0.37741(13) 0.5455(2) 0.0410(4) Uani 1 1 d .
C3 C 0.83686(10) 0.42705(12) 0.6049(2) 0.0336(4) Uani 1 1 d .
C4 C 0.78841(10) 0.40105(10) 0.7681(2) 0.0324(4) Uani 1 1 d .
H4A H 0.8280 0.3715 0.8605 0.039 Uiso 1 1 calc R
H4B H 0.7472 0.3531 0.7263 0.039 Uiso 1 1 calc R
C5 C 0.74012(9) 0.47779(9) 0.86987(18) 0.0262(3) Uani 1 1 d .
C6 C 0.79878(9) 0.54015(10) 0.99178(18) 0.0273(3) Uani 1 1 d .
C7 C 0.76868(10) 0.58446(10) 1.14569(19) 0.0308(3) Uani 1 1 d .
H7 H 0.7132 0.5723 1.1783 0.037 Uiso 1 1 calc R
C8 C 0.81785(11) 0.64550(11) 1.2514(2) 0.0362(4) Uani 1 1 d .
H8 H 0.7960 0.6748 1.3554 0.043 Uiso 1 1 calc R
C9 C 0.89834(11) 0.66396(12) 1.2068(2) 0.0410(4) Uani 1 1 d .
H9 H 0.9320 0.7067 1.2782 0.049 Uiso 1 1 calc R
C10 C 0.92990(11) 0.61978(12) 1.0569(2) 0.0436(4) Uani 1 1 d .
H10 H 0.9858 0.6316 1.0264 0.052 Uiso 1 1 calc R
C11 C 0.88063(10) 0.55837(11) 0.9508(2) 0.0360(4) Uani 1 1 d .
H11 H 0.9033 0.5284 0.8485 0.043 Uiso 1 1 calc R
C12 C 0.68131(9) 0.42418(9) 0.99483(18) 0.0269(3) Uani 1 1 d .
C13 C 0.59495(10) 0.42330(10) 0.96822(19) 0.0310(4) Uani 1 1 d .
H13 H 0.5686 0.4594 0.8716 0.037 Uiso 1 1 calc R
C14 C 0.54581(11) 0.37040(11) 1.0808(2) 0.0375(4) Uani 1 1 d .
H14 H 0.4867 0.3704 1.0594 0.045 Uiso 1 1 calc R
C15 C 0.58257(12) 0.31829(11) 1.2227(2) 0.0390(4) Uani 1 1 d .
H15 H 0.5492 0.2819 1.2988 0.047 Uiso 1 1 calc R
C16 C 0.66852(11) 0.31950(10) 1.2530(2) 0.0363(4) Uani 1 1 d .
H16 H 0.6943 0.2844 1.3517 0.044 Uiso 1 1 calc R
C17 C 0.71753(11) 0.37131(10) 1.14070(19) 0.0323(4) Uani 1 1 d .
H17 H 0.7766 0.3710 1.1630 0.039 Uiso 1 1 calc R
C18 C 0.68975(9) 0.53718(10) 0.72519(17) 0.0253(3) Uani 1 1 d .
C19 C 0.68962(10) 0.63299(10) 0.72909(19) 0.0297(3) Uani 1 1 d .
H19 H 0.7223 0.6644 0.8234 0.036 Uiso 1 1 calc R
C20 C 0.64255(10) 0.68418(11) 0.5976(2) 0.0349(4) Uani 1 1 d .
H20 H 0.6434 0.7499 0.6029 0.042 Uiso 1 1 calc R
C21 C 0.59467(10) 0.64007(11) 0.4595(2) 0.0364(4) Uani 1 1 d .
H21 H 0.5619 0.6751 0.3708 0.044 Uiso 1 1 calc R
C22 C 0.59484(10) 0.54491(11) 0.45153(19) 0.0352(4) Uani 1 1 d .
H22 H 0.5626 0.5140 0.3558 0.042 Uiso 1 1 calc R
C23 C 0.64174(10) 0.49406(11) 0.58218(19) 0.0322(4) Uani 1 1 d .
H23 H 0.6413 0.4284 0.5746 0.039 Uiso 1 1 calc R
H3 H 0.8226(11) 0.4838(13) 0.543(3) 0.052(5) Uiso 1 1 d .
H2 H 0.9106(12) 0.3163(14) 0.606(3) 0.061(6) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C1 126.49(17)
C3 C2 H2 118.0(11)
C1 C2 H2 115.1(11)
C2 C3 C4 123.84(15)
C2 C3 H3 118.6(11)
C4 C3 H3 117.5(11)
C3 C4 C5 119.33(13)
C3 C4 H4A 107.5
C5 C4 H4A 107.5
C3 C4 H4B 107.5
C5 C4 H4B 107.5
H4A C4 H4B 107.0
C6 C5 C18 109.87(11)
C6 C5 C12 109.07(11)
C18 C5 C12 111.29(12)
C6 C5 C4 112.56(12)
C18 C5 C4 109.03(11)
C12 C5 C4 104.96(11)
C11 C6 C7 117.50(13)
C11 C6 C5 122.59(12)
C7 C6 C5 119.84(13)
C8 C7 C6 121.46(14)
C8 C7 H7 119.3
C6 C7 H7 119.3
C9 C8 C7 120.22(15)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 119.32(15)
C8 C9 H9 120.3
C10 C9 H9 120.3
C9 C10 C11 120.51(16)
C9 C10 H10 119.7
C11 C10 H10 119.7
C6 C11 C10 120.97(15)
C6 C11 H11 119.5
C10 C11 H11 119.5
C13 C12 C17 117.61(13)
C13 C12 C5 124.05(12)
C17 C12 C5 118.31(13)
C12 C13 C14 121.20(14)
C12 C13 H13 119.4
C14 C13 H13 119.4
C15 C14 C13 120.36(16)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 119.20(15)
C14 C15 H15 120.4
C16 C15 H15 120.4
C15 C16 C17 120.61(15)
C15 C16 H16 119.7
C17 C16 H16 119.7
C16 C17 C12 121.00(15)
C16 C17 H17 119.5
C12 C17 H17 119.5
C19 C18 C23 117.32(13)
C19 C18 C5 122.89(12)
C23 C18 C5 119.80(13)
C18 C19 C20 121.25(13)
C18 C19 H19 119.4
C20 C19 H19 119.4
C21 C20 C19 120.38(14)
C21 C20 H20 119.8
C19 C20 H20 119.8
C22 C21 C20 119.32(14)
C22 C21 H21 120.3
C20 C21 H21 120.3
C21 C22 C23 120.26(14)
C21 C22 H22 119.9
C23 C22 H22 119.9
C22 C23 C18 121.46(14)
C22 C23 H23 119.3
C18 C23 H23 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.492(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.310(2)
C2 H2 1.00(2)
C3 C4 1.502(2)
C3 H3 0.954(19)
C4 C5 1.562(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5395(19)
C5 C18 1.5429(18)
C5 C12 1.5531(19)
C6 C11 1.387(2)
C6 C7 1.398(2)
C7 C8 1.382(2)
C7 H7 0.9500
C8 C9 1.374(2)
C8 H8 0.9500
C9 C10 1.382(2)
C9 H9 0.9500
C10 C11 1.387(2)
C10 H10 0.9500
C11 H11 0.9500
C12 C13 1.384(2)
C12 C17 1.400(2)
C13 C14 1.396(2)
C13 H13 0.9500
C14 C15 1.376(2)
C14 H14 0.9500
C15 C16 1.380(2)
C15 H15 0.9500
C16 C17 1.384(2)
C16 H16 0.9500
C17 H17 0.9500
C18 C19 1.383(2)
C18 C23 1.3979(19)
C19 C20 1.390(2)
C19 H19 0.9500
C20 C21 1.378(2)
C20 H20 0.9500
C21 C22 1.375(2)
C21 H21 0.9500
C22 C23 1.382(2)
C22 H22 0.9500
C23 H23 0.9500
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
C1 C2 C3 C4 177.01(16)
C2 C3 C4 C5 158.46(16)
C3 C4 C5 C6 -75.00(17)
C3 C4 C5 C18 47.18(18)
C3 C4 C5 C12 166.50(13)
C18 C5 C6 C11 -91.95(16)
C12 C5 C6 C11 145.82(14)
C4 C5 C6 C11 29.76(18)
C18 C5 C6 C7 84.92(15)
C12 C5 C6 C7 -37.32(17)
C4 C5 C6 C7 -153.38(13)
C11 C6 C7 C8 1.2(2)
C5 C6 C7 C8 -175.84(13)
C6 C7 C8 C9 -0.1(2)
C7 C8 C9 C10 -1.0(2)
C8 C9 C10 C11 0.9(3)
C7 C6 C11 C10 -1.3(2)
C5 C6 C11 C10 175.67(14)
C9 C10 C11 C6 0.3(3)
C6 C5 C12 C13 126.96(14)
C18 C5 C12 C13 5.58(18)
C4 C5 C12 C13 -112.21(15)
C6 C5 C12 C17 -54.84(16)
C18 C5 C12 C17 -176.22(12)
C4 C5 C12 C17 65.99(15)
C17 C12 C13 C14 -1.0(2)
C5 C12 C13 C14 177.17(13)
C12 C13 C14 C15 0.6(2)
C13 C14 C15 C16 0.4(2)
C14 C15 C16 C17 -0.9(2)
C15 C16 C17 C12 0.5(2)
C13 C12 C17 C16 0.5(2)
C5 C12 C17 C16 -177.78(13)
C6 C5 C18 C19 -9.37(18)
C12 C5 C18 C19 111.54(15)
C4 C5 C18 C19 -133.16(14)
C6 C5 C18 C23 170.48(13)
C12 C5 C18 C23 -68.61(16)
C4 C5 C18 C23 46.70(17)
C23 C18 C19 C20 1.0(2)
C5 C18 C19 C20 -179.16(13)
C18 C19 C20 C21 0.0(2)
C19 C20 C21 C22 -0.9(2)
C20 C21 C22 C23 0.8(2)
C21 C22 C23 C18 0.2(2)
C19 C18 C23 C22 -1.1(2)
C5 C18 C23 C22 179.07(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659744
