#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:50:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178536 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/42/4064219.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_4064219
loop_
_publ_author_name
'Martin, Thomas A.'
'Ellul, Charles E.'
'Mahon, Mary F.'
'Warren, Mark E.'
'Allan, David'
'Whittlesey, Michael K.'
_publ_section_title
;
 Neutral and Cationic Mono- and Bis-N-heterocyclic Carbene Complexes
 Derived From Manganese and Rhenium Carbonyl Precursors
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2200
_journal_paper_doi               10.1021/om1011853
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C31 H36 Br Mn N2 O4'
_chemical_formula_weight         635.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 106.589(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8080(2)
_cell_length_b                   19.7330(4)
_cell_length_c                   9.3240(2)
_cell_measurement_reflns_used    61155
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1553.14(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            32262
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0403
_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)+(0.0370P)²+0.9441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                2941
_reflns_number_total             3661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1011853_si_001.cif
_cod_data_source_block           k10mkw5
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               4064219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57075(6) 0.2500 0.49172(8) 0.04706(15) Uani 0.80 2 d SP A 1
Br1A Br 0.5312(5) 0.2500 0.1219(5) 0.0462(9) Uani 0.20 2 d SP A 2
Mn1 Mn 0.33468(5) 0.2500 0.26510(5) 0.02972(14) Uani 1 2 d SD . .
O1 O 0.0652(3) 0.2500 -0.0094(3) 0.0440(6) Uani 1 2 d SD . .
O2 O 0.3913(2) 0.39931(8) 0.2480(2) 0.0482(4) Uani 1 1 d D . .
O3 O 0.5581(10) 0.2500 0.0761(8) 0.056(2) Uani 0.80 2 d SPD A 1
N1 N 0.09994(19) 0.19590(8) 0.43333(19) 0.0256(4) Uani 1 1 d . . .
C1 C 0.1676(4) 0.2500 0.0968(4) 0.0331(7) Uani 1 2 d SD A .
C2 C 0.3591(2) 0.34428(12) 0.2620(3) 0.0352(5) Uani 1 1 d D A .
C3 C 0.4714(7) 0.2500 0.1509(8) 0.0385(14) Uani 0.80 2 d SPD A 1
C4 C 0.1738(3) 0.2500 0.3903(3) 0.0254(6) Uani 1 2 d S . .
C5 C -0.0170(2) 0.21624(11) 0.4964(2) 0.0318(5) Uani 1 1 d . . .
H5 H -0.0844 0.1876 0.5328 0.038 Uiso 1 1 calc R . .
C6 C 0.1353(2) 0.12463(10) 0.4247(2) 0.0266(4) Uani 1 1 d . A .
C7 C 0.2529(2) 0.09588(11) 0.5442(2) 0.0304(4) Uani 1 1 d . . .
C8 C 0.2812(3) 0.02655(11) 0.5350(3) 0.0364(5) Uani 1 1 d . A .
H8 H 0.3627 0.0055 0.6113 0.044 Uiso 1 1 calc R . .
C9 C 0.1922(3) -0.01190(11) 0.4165(3) 0.0389(5) Uani 1 1 d . . .
H9 H 0.2120 -0.0591 0.4132 0.047 Uiso 1 1 calc R A .
C10 C 0.0755(3) 0.01768(11) 0.3034(3) 0.0354(5) Uani 1 1 d . A .
H10 H 0.0148 -0.0096 0.2236 0.042 Uiso 1 1 calc R . .
C11 C 0.0443(2) 0.08721(11) 0.3034(2) 0.0289(4) Uani 1 1 d . . .
C12 C -0.0845(2) 0.11863(11) 0.1767(2) 0.0317(5) Uani 1 1 d . A .
H12 H -0.0728 0.1690 0.1847 0.038 Uiso 1 1 calc R . .
C13 C -0.2494(3) 0.10025(14) 0.1898(3) 0.0440(6) Uani 1 1 d . . .
H13A H -0.2618 0.0509 0.1868 0.066 Uiso 1 1 calc R A .
H13B H -0.3306 0.1205 0.1062 0.066 Uiso 1 1 calc R . .
H13C H -0.2609 0.1176 0.2845 0.066 Uiso 1 1 calc R . .
C14 C -0.0696(3) 0.09725(13) 0.0235(3) 0.0412(5) Uani 1 1 d . . .
H14A H -0.0981 0.0493 0.0062 0.062 Uiso 1 1 calc R A .
H14B H 0.0399 0.1039 0.0210 0.062 Uiso 1 1 calc R . .
H14C H -0.1409 0.1248 -0.0546 0.062 Uiso 1 1 calc R . .
C15 C 0.3401(3) 0.13655(12) 0.6804(3) 0.0362(5) Uani 1 1 d . A .
H15 H 0.3366 0.1852 0.6499 0.043 Uiso 1 1 calc R . .
C16 C 0.2564(3) 0.13058(15) 0.8027(3) 0.0508(6) Uani 1 1 d . . .
H16A H 0.1455 0.1445 0.7626 0.076 Uiso 1 1 calc R A .
H16B H 0.3092 0.1599 0.8870 0.076 Uiso 1 1 calc R . .
H16C H 0.2609 0.0835 0.8370 0.076 Uiso 1 1 calc R . .
C17 C 0.5149(3) 0.11631(16) 0.7427(3) 0.0550(7) Uani 1 1 d . . .
H17A H 0.5220 0.0711 0.7877 0.082 Uiso 1 1 calc R A .
H17B H 0.5694 0.1491 0.8189 0.082 Uiso 1 1 calc R . .
H17C H 0.5649 0.1158 0.6614 0.082 Uiso 1 1 calc R . .
O3A O 0.600(2) 0.2500 0.5493(19) 0.078(9) Uiso 0.20 2 d SPD A 2
C3A C 0.496(3) 0.2500 0.443(2) 0.086(9) Uiso 0.20 2 d SPD A 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Mn1 C3 90.1(2) . .
C1 Mn1 C3A 176.5(11) . .
C3 Mn1 C3A 93.4(11) . .
C1 Mn1 C2 93.14(7) . .
C3 Mn1 C2 83.86(7) . .
C3A Mn1 C2 87.25(14) . .
C1 Mn1 C2 93.14(7) . 4_565
C3 Mn1 C2 83.86(7) . 4_565
C3A Mn1 C2 87.25(14) . 4_565
C2 Mn1 C2 166.21(13) . 4_565
C1 Mn1 C4 88.37(12) . .
C3 Mn1 C4 178.5(2) . .
C3A Mn1 C4 88.1(11) . .
C2 Mn1 C4 96.22(6) . .
C2 Mn1 C4 96.22(6) 4_565 .
C1 Mn1 Br1A 93.02(14) . .
C3 Mn1 Br1A 2.9(2) . .
C3A Mn1 Br1A 90.5(11) . .
C2 Mn1 Br1A 83.71(6) . .
C2 Mn1 Br1A 83.71(6) 4_565 .
C4 Mn1 Br1A 178.61(13) . .
C1 Mn1 Br1 178.14(10) . .
C3 Mn1 Br1 88.0(2) . .
C3A Mn1 Br1 5.4(11) . .
C2 Mn1 Br1 86.67(7) . .
C2 Mn1 Br1 86.67(7) 4_565 .
C4 Mn1 Br1 93.49(8) . .
Br1A Mn1 Br1 85.12(10) . .
C4 N1 C5 111.86(17) . .
C4 N1 C6 127.85(17) . .
C5 N1 C6 120.24(17) . .
O1 C1 Mn1 178.9(3) . .
O2 C2 Mn1 168.96(19) . .
O3 C3 Mn1 179.3(8) . .
N1 C4 N1 102.5(2) . 4_565
N1 C4 Mn1 128.49(11) . .
N1 C4 Mn1 128.49(11) 4_565 .
C5 C5 N1 106.87(11) 4_565 .
C5 C5 H5 126.6 4_565 .
N1 C5 H5 126.6 . .
C11 C6 C7 123.45(19) . .
C11 C6 N1 118.44(18) . .
C7 C6 N1 117.98(18) . .
C8 C7 C6 116.8(2) . .
C8 C7 C15 120.93(19) . .
C6 C7 C15 122.25(19) . .
C9 C8 C7 121.0(2) . .
C9 C8 H8 119.5 . .
C7 C8 H8 119.5 . .
C10 C9 C8 120.6(2) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C9 C10 C11 121.3(2) . .
C9 C10 H10 119.3 . .
C11 C10 H10 119.3 . .
C6 C11 C10 116.84(19) . .
C6 C11 C12 122.92(19) . .
C10 C11 C12 120.24(19) . .
C11 C12 C14 111.69(18) . .
C11 C12 C13 110.84(18) . .
C14 C12 C13 110.15(19) . .
C11 C12 H12 108.0 . .
C14 C12 H12 108.0 . .
C13 C12 H12 108.0 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C7 C15 C16 110.39(19) . .
C7 C15 C17 113.2(2) . .
C16 C15 C17 110.0(2) . .
C7 C15 H15 107.7 . .
C16 C15 H15 107.7 . .
C17 C15 H15 107.7 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O3A C3A Mn1 177(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Mn1 2.5059(8) .
Br1A Mn1 2.470(4) .
Mn1 C1 1.819(3) .
Mn1 C3 1.821(6) .
Mn1 C3A 1.849(13) .
Mn1 C2 1.874(2) .
Mn1 C2 1.874(2) 4_565
Mn1 C4 2.077(3) .
O1 C1 1.133(4) .
O2 C2 1.139(3) .
O3 C3 1.172(7) .
N1 C4 1.369(2) .
N1 C5 1.383(3) .
N1 C6 1.448(2) .
C4 N1 1.369(2) 4_565
C5 C5 1.332(4) 4_565
C5 H5 0.9500 .
C6 C11 1.396(3) .
C6 C7 1.406(3) .
C7 C8 1.398(3) .
C7 C15 1.513(3) .
C8 C9 1.385(3) .
C8 H8 0.9500 .
C9 C10 1.375(3) .
C9 H9 0.9500 .
C10 C11 1.399(3) .
C10 H10 0.9500 .
C11 C12 1.518(3) .
C12 C14 1.530(3) .
C12 C13 1.535(3) .
C12 H12 1.0000 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.529(3) .
C15 C17 1.536(3) .
C15 H15 1.0000 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
O3A C3A 1.143(14) .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C3 Mn1 C1 O1 -0.001(8) . .
C3A Mn1 C1 O1 179.999(7) . .
C2 Mn1 C1 O1 83.85(7) . .
C2 Mn1 C1 O1 -83.86(7) 4_565 .
C4 Mn1 C1 O1 179.999(8) . .
Br1A Mn1 C1 O1 -0.001(7) . .
Br1 Mn1 C1 O1 -0.001(9) . .
C1 Mn1 C2 O2 -94.2(11) . .
C3 Mn1 C2 O2 -4.3(11) . .
C3A Mn1 C2 O2 89.4(15) . .
C2 Mn1 C2 O2 22.8(16) 4_565 .
C4 Mn1 C2 O2 177.1(11) . .
Br1A Mn1 C2 O2 -1.5(11) . .
Br1 Mn1 C2 O2 84.0(11) . .
C1 Mn1 C3 O3 0.00(4) . .
C3A Mn1 C3 O3 180.00(4) . .
C2 Mn1 C3 O3 -93.14(9) . .
C2 Mn1 C3 O3 93.14(9) 4_565 .
C4 Mn1 C3 O3 0.00(4) . .
Br1A Mn1 C3 O3 180.00(4) . .
Br1 Mn1 C3 O3 180.00(4) . .
C5 N1 C4 N1 1.5(3) . 4_565
C6 N1 C4 N1 -175.95(13) . 4_565
C5 N1 C4 Mn1 -170.90(18) . .
C6 N1 C4 Mn1 11.7(3) . .
C1 Mn1 C4 N1 85.3(2) . .
C3 Mn1 C4 N1 85.3(2) . .
C3A Mn1 C4 N1 -94.7(2) . .
C2 Mn1 C4 N1 178.2(2) . .
C2 Mn1 C4 N1 -7.7(2) 4_565 .
Br1A Mn1 C4 N1 -94.7(2) . .
Br1 Mn1 C4 N1 -94.7(2) . .
C1 Mn1 C4 N1 -85.3(2) . 4_565
C3 Mn1 C4 N1 -85.3(2) . 4_565
C3A Mn1 C4 N1 94.7(2) . 4_565
C2 Mn1 C4 N1 7.7(2) . 4_565
C2 Mn1 C4 N1 -178.2(2) 4_565 4_565
Br1A Mn1 C4 N1 94.7(2) . 4_565
Br1 Mn1 C4 N1 94.7(2) . 4_565
C4 N1 C5 C5 -0.98(18) . 4_565
C6 N1 C5 C5 176.69(14) . 4_565
C4 N1 C6 C11 -97.8(3) . .
C5 N1 C6 C11 84.9(2) . .
C4 N1 C6 C7 86.2(3) . .
C5 N1 C6 C7 -91.0(2) . .
C11 C6 C7 C8 2.3(3) . .
N1 C6 C7 C8 178.09(18) . .
C11 C6 C7 C15 -174.71(19) . .
N1 C6 C7 C15 1.0(3) . .
C6 C7 C8 C9 -2.6(3) . .
C15 C7 C8 C9 174.5(2) . .
C7 C8 C9 C10 1.2(4) . .
C8 C9 C10 C11 0.8(4) . .
C7 C6 C11 C10 -0.5(3) . .
N1 C6 C11 C10 -176.27(18) . .
C7 C6 C11 C12 178.76(18) . .
N1 C6 C11 C12 3.0(3) . .
C9 C10 C11 C6 -1.1(3) . .
C9 C10 C11 C12 179.6(2) . .
C6 C11 C12 C14 131.6(2) . .
C10 C11 C12 C14 -49.1(3) . .
C6 C11 C12 C13 -105.1(2) . .
C10 C11 C12 C13 74.1(3) . .
C8 C7 C15 C16 -84.5(3) . .
C6 C7 C15 C16 92.4(3) . .
C8 C7 C15 C17 39.3(3) . .
C6 C7 C15 C17 -143.8(2) . .
C1 Mn1 C3A O3A 180.00(7) . .
C3 Mn1 C3A O3A 0.00(7) . .
C2 Mn1 C3A O3A -83.67(12) . .
C2 Mn1 C3A O3A 83.67(12) 4_565 .
C4 Mn1 C3A O3A 180.00(7) . .
Br1A Mn1 C3A O3A 0.00(7) . .
Br1 Mn1 C3A O3A 0.00(7) . .
