#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/82/2228246.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_2228246
loop_
_publ_author_name
'Nielson, Alastair J.'
'Waters, Joyce M.'
_publ_section_title
;
 (2,2'-Bipyridine-κ²N,N')[2-tert-butylanilinato(2{-})]dichloridooxidomolybdenum(VI)
 dichloromethane hemisolvate
;
_journal_coeditor_code           BV2152
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1659
_journal_page_last               m1660
_journal_paper_doi               10.1107/S1600536810047392
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Mo (C10 H13 N) Cl2 O (C10 H8 N2)], 0.5C H2 Cl2'
_chemical_formula_moiety         'C20 H21 Cl2 Mo N3 O, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C20.5 H22 Cl3 Mo N3 O'
_chemical_formula_weight         528.7
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')[2-tert-
butylanilinato(2-)]dichloridooxidomolybdenum(VI) dichloromethane hemisolvate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.4207(2)
_cell_length_b                   14.96570(10)
_cell_length_c                   16.52370(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     4307.94(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Siemens SMART'
_diffrn_measurement_method       'Area detector ω scan'
_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  0.0835
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            40908
_diffrn_reflns_theta_full        26.55
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.998
_exptl_absorpt_correction_T_max  0.9630
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.636
_refine_diff_density_min         -1.543
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0540P)²+1.7768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                3438
_reflns_number_total             4459
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2152.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C20.5 H22 Cl3 Mo1 N3 O1'
_cod_database_code               2228246
_cod_database_fobs_code          2228246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
Mo Mo1 0.353791(15) 0.84420(2) 0.150599(16) 0.02018(11) Uani d . 1 . .
Cl Cl1 0.31084(5) 0.72649(6) 0.06725(5) 0.0299(2) Uani d . 1 . .
Cl Cl2 0.41115(5) 0.98134(6) 0.19018(5) 0.0291(2) Uani d . 1 . .
N N1 0.26663(15) 0.87982(19) 0.18979(16) 0.0208(6) Uani d . 1 . .
N N2 0.46431(15) 0.83274(18) 0.08033(16) 0.0218(6) Uani d . 1 . .
N N3 0.34325(15) 0.91836(19) 0.03034(16) 0.0226(6) Uani d . 1 . .
O O1 0.39213(13) 0.77987(16) 0.22394(13) 0.0257(5) Uani d . 1 . .
C C1 0.52275(19) 0.7863(2) 0.1095(2) 0.0269(8) Uani d . 1 . .
H H1 0.5178 0.7587 0.1610 0.032 Uiso calc R 1 . .
C C2 0.5900(2) 0.7769(3) 0.0679(2) 0.0298(8) Uani d . 1 . .
H H2 0.6311 0.7430 0.0900 0.036 Uiso calc R 1 . .
C C3 0.5975(2) 0.8169(3) -0.0060(2) 0.0300(8) Uani d . 1 . .
H H3 0.6436 0.8111 -0.0362 0.036 Uiso calc R 1 . .
C C4 0.53740(19) 0.8656(2) -0.0355(2) 0.0258(8) Uani d . 1 . .
H H4 0.5416 0.8943 -0.0865 0.031 Uiso calc R 1 . .
C C5 0.47099(19) 0.8728(2) 0.00858(18) 0.0197(7) Uani d . 1 . .
C C6 0.40356(18) 0.9217(2) -0.01916(18) 0.0197(7) Uani d . 1 . .
C C7 0.4003(2) 0.9672(2) -0.0908(2) 0.0258(8) Uani d . 1 . .
H H7 0.4441 0.9698 -0.1250 0.031 Uiso calc R 1 . .
C C8 0.3339(2) 1.0088(2) -0.1132(2) 0.0282(8) Uani d . 1 . .
H H8 0.3311 1.0415 -0.1623 0.034 Uiso calc R 1 . .
C C9 0.2717(2) 1.0023(3) -0.0635(2) 0.0327(9) Uani d . 1 . .
H H9 0.2243 1.0289 -0.0784 0.039 Uiso calc R 1 . .
C C10 0.2782(2) 0.9575(3) 0.0072(2) 0.0300(8) Uani d . 1 . .
H H10 0.2347 0.9539 0.0417 0.036 Uiso calc R 1 . .
C C11 0.20734(19) 0.9275(2) 0.22186(19) 0.0225(7) Uani d . 1 . .
C C12 0.2068(2) 1.0188(2) 0.2053(2) 0.0341(9) Uani d . 1 . .
H H12 0.2446 1.0435 0.1705 0.041 Uiso calc R 1 . .
C C13 0.1527(2) 1.0727(3) 0.2388(3) 0.0425(10) Uani d . 1 . .
H H13 0.1533 1.1352 0.2290 0.051 Uiso calc R 1 . .
C C14 0.0974(2) 1.0355(3) 0.2866(3) 0.0415(10) Uani d . 1 . .
H H14 0.0589 1.0725 0.3097 0.050 Uiso calc R 1 . .
C C15 0.0967(2) 0.9464(3) 0.3014(2) 0.0327(9) Uani d . 1 . .
H H15 0.0568 0.9227 0.3341 0.039 Uiso calc R 1 . .
C C16 0.15120(18) 0.8890(2) 0.27117(19) 0.0219(7) Uani d . 1 . .
C C17 0.15032(18) 0.7900(2) 0.2892(2) 0.0241(7) Uani d . 1 . .
C C18 0.2222(2) 0.7626(3) 0.3349(2) 0.0294(8) Uani d . 1 . .
H H18A 0.2676 0.7779 0.3028 0.044 Uiso calc R 1 . .
H H18B 0.2212 0.6980 0.3446 0.044 Uiso calc R 1 . .
H H18C 0.2241 0.7941 0.3868 0.044 Uiso calc R 1 . .
C C19 0.1439(2) 0.7378(3) 0.2113(2) 0.0324(9) Uani d . 1 . .
H H19A 0.0978 0.7567 0.1820 0.049 Uiso calc R 1 . .
H H19B 0.1404 0.6738 0.2236 0.049 Uiso calc R 1 . .
H H19C 0.1893 0.7489 0.1778 0.049 Uiso calc R 1 . .
C C20 0.0821(2) 0.7650(3) 0.3419(2) 0.0374(10) Uani d . 1 . .
H H20A 0.0853 0.7971 0.3935 0.056 Uiso calc R 1 . .
H H20B 0.0826 0.7005 0.3520 0.056 Uiso calc R 1 . .
H H20C 0.0344 0.7813 0.3141 0.056 Uiso calc R 1 . .
C C21 0.4547(10) 0.5417(12) 0.0336(9) 0.088(5) Uani d P 0.50 . 1
H H21A 0.428(7) 0.558(9) 0.007(7) 0.080 Uiso d P 0.50 A 1
H H21B 0.452(7) 0.562(8) 0.074(7) 0.080 Uiso d P 0.50 B 1
Cl Cl3 0.4319(3) 0.4302(3) 0.0347(4) 0.0822(14) Uani d P 0.50 . 1
Cl Cl4 0.5425(4) 0.5541(6) -0.0196(6) 0.162(4) Uani d P 0.50 . 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 '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'
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
O1 Mo1 N1 . . 104.71(12) ?
O1 Mo1 N2 . . 89.34(10) ?
N1 Mo1 N2 . . 164.37(11) ?
O1 Mo1 N3 . . 159.24(10) ?
N1 Mo1 N3 . . 96.03(11) ?
N2 Mo1 N3 . . 69.97(9) ?
O1 Mo1 Cl1 . . 96.83(8) ?
N1 Mo1 Cl1 . . 99.78(9) ?
N2 Mo1 Cl1 . . 85.03(7) ?
N3 Mo1 Cl1 . . 80.17(7) ?
O1 Mo1 Cl2 . . 97.41(8) ?
N1 Mo1 Cl2 . . 90.00(9) ?
N2 Mo1 Cl2 . . 81.28(7) ?
N3 Mo1 Cl2 . . 81.57(7) ?
Cl1 Mo1 Cl2 . . 160.08(3) ?
C11 N1 Mo1 . . 165.8(2) ?
C1 N2 C5 . . 119.5(3) ?
C1 N2 Mo1 . . 120.6(2) ?
C5 N2 Mo1 . . 119.9(2) ?
C10 N3 C6 . . 118.5(3) ?
C10 N3 Mo1 . . 122.2(2) ?
C6 N3 Mo1 . . 119.3(2) ?
N2 C1 C2 . . 122.0(3) ?
N2 C1 H1 . . 119.0 ?
C2 C1 H1 . . 119.0 ?
C3 C2 C1 . . 119.1(3) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C4 C3 C2 . . 118.7(3) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 120.0(3) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
N2 C5 C4 . . 120.7(3) ?
N2 C5 C6 . . 115.8(3) ?
C4 C5 C6 . . 123.5(3) ?
N3 C6 C7 . . 121.2(3) ?
N3 C6 C5 . . 115.0(3) ?
C7 C6 C5 . . 123.8(3) ?
C8 C7 C6 . . 119.8(3) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C9 . . 118.6(3) ?
C7 C8 H8 . . 120.7 ?
C9 C8 H8 . . 120.7 ?
C10 C9 C8 . . 119.3(3) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
N3 C10 C9 . . 122.6(3) ?
N3 C10 H10 . . 118.7 ?
C9 C10 H10 . . 118.7 ?
N1 C11 C12 . . 116.2(3) ?
N1 C11 C16 . . 122.8(3) ?
C12 C11 C16 . . 121.0(3) ?
C13 C12 C11 . . 120.5(4) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 118.9(4) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C15 C14 C13 . . 120.8(4) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 122.9(4) ?
C14 C15 H15 . . 118.5 ?
C16 C15 H15 . . 118.5 ?
C15 C16 C11 . . 115.9(3) ?
C15 C16 C17 . . 122.3(3) ?
C11 C16 C17 . . 121.8(3) ?
C19 C17 C16 . . 109.9(3) ?
C19 C17 C18 . . 110.2(3) ?
C16 C17 C18 . . 110.7(3) ?
C19 C17 C20 . . 107.6(3) ?
C16 C17 C20 . . 111.2(3) ?
C18 C17 C20 . . 107.1(3) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
Cl3 C21 Cl4 . . 107.9(9) ?
Cl4 C21 H21A 5_665 . 106(10) ?
Cl3 C21 H21A . . 101(10) ?
Cl4 C21 H21A . . 103(10) ?
Cl4 C21 H21B 5_665 . 123(10) ?
Cl3 C21 H21B . . 112(10) ?
Cl4 C21 H21B . . 118(10) ?
H21A C21 H21B . . 113(10) ?
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
Mo1 O1 . 1.686(2) ?
Mo1 N1 . 1.735(3) ?
Mo1 N2 . 2.255(3) ?
Mo1 N3 . 2.283(3) ?
Mo1 Cl1 . 2.3580(9) ?
Mo1 Cl2 . 2.3745(9) ?
N1 C11 . 1.363(4) ?
N2 C1 . 1.323(4) ?
N2 C5 . 1.334(4) ?
N3 C10 . 1.332(4) ?
N3 C6 . 1.332(4) ?
C1 C2 . 1.366(5) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.365(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.365(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.371(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.458(4) ?
C6 C7 . 1.367(4) ?
C7 C8 . 1.363(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.363(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.350(5) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.393(5) ?
C11 C16 . 1.397(4) ?
C12 C13 . 1.359(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.364(6) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.356(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.375(5) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.511(5) ?
C17 C19 . 1.510(5) ?
C17 C18 . 1.519(5) ?
C17 C20 . 1.520(4) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 Cl4 5_665 1.453(17) ?
C21 Cl3 . 1.715(19) ?
C21 Cl4 . 1.77(2) ?
C21 H21A . 0.70(12) ?
C21 H21B . 0.74(11) ?
Cl3 Cl4 5_665 0.563(9) ?
Cl4 Cl3 5_665 0.563(9) ?
Cl4 C21 5_665 1.453(17) ?
Cl4 Cl4 5_665 2.287(12) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C18 H18A O1 . 0.98 2.53 3.492(4) 167
C18 H18A N1 . 0.98 2.41 3.070(5) 124
C19 H19C Cl1 . 0.98 2.82 3.762(4) 162
C19 H19C N1 . 0.98 2.39 3.036(5) 123
