#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:10:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178739 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/50/4085008.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_4085008
loop_
_publ_author_name
'Vollmer, Matthew V.'
'Machan, Charles W.'
'Clark, Melissa L.'
'Antholine, William E.'
'Agarwal, Jay'
'Schaefer, 3rd, Henry F'
'Kubiak, Clifford P.'
'Walensky, Justin R.'
_publ_section_title
;
 Synthesis, Spectroscopy, and Electrochemistry of (α-Diimine)M(CO)3Br, M
 = Mn, Re, Complexes: Ligands Isoelectronic to Bipyridyl Show Differences
 in CO2 Reduction.
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              3
_journal_page_last               12
_journal_paper_doi               10.1021/om500838z
_journal_volume                  34
_journal_year                    2014
_chemical_formula_moiety         'C31 H40 Br N2 O3, C H2 Cl2, C2 H3 N'
_chemical_formula_sum            'C34 H45 Br Cl2 N3 O3 Re'
_chemical_formula_weight         880.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.1760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1468(15)
_cell_length_b                   16.477(2)
_cell_length_c                   11.2970(17)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     1846.2(4)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21526
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.844
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    4.553
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       Block
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0164
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0214P)²+1.2668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4184
_reflns_number_total             4368
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om500838z_si_003.cif
_cod_data_source_block           MAM30
_cod_depositor_comments
;Adding full bibliography for 4085006--4085014.cif.

 Adding full bibliography for 4085006--4085014.cif.
;
_cod_original_cell_volume        1846.2(5)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4085008
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.280
_shelx_estimated_absorpt_t_max   0.548
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Re1 Re 0.67970(2) 0.2500 0.89208(2) 0.01888(4) Uani 1 2 d S T P
Br1 Br 0.89368(3) 0.2500 0.79494(3) 0.02634(6) Uani 1 2 d S T P
Cl1 Cl -0.1344(2) 0.33608(11) 0.37692(19) 0.1690(8) Uani 1 1 d . . .
O1 O 0.81720(17) 0.11773(11) 1.06736(16) 0.0424(4) Uani 1 1 d . . .
O3 O 0.4642(2) 0.2500 1.04499(19) 0.0333(5) Uani 1 2 d S T P
N1 N 0.58765(15) 0.17082(9) 0.74415(14) 0.0203(3) Uani 1 1 d . . .
N3 N 0.2111(3) 0.2500 0.3532(3) 0.0536(8) Uani 1 2 d S T P
C1 C 0.7656(2) 0.16759(12) 1.00238(18) 0.0271(4) Uani 1 1 d . . .
C3 C 0.5401(3) 0.2500 0.9813(2) 0.0244(5) Uani 1 2 d S T P
C4 C 0.55681(18) 0.20469(11) 0.63838(16) 0.0222(4) Uani 1 1 d . . .
C6 C 0.5122(2) 0.16044(13) 0.52096(17) 0.0310(4) Uani 1 1 d . . .
H6A H 0.5058 0.1022 0.5368 0.047 Uiso 1 1 calc R U .
H6B H 0.5778 0.1693 0.4698 0.047 Uiso 1 1 calc R U .
H6C H 0.4237 0.1808 0.4794 0.047 Uiso 1 1 calc R U .
C7 C 0.55841(19) 0.08454(11) 0.75462(16) 0.0225(4) Uani 1 1 d . . .
C8 C 0.6523(2) 0.02491(12) 0.74091(18) 0.0275(4) Uani 1 1 d . . .
C9 C 0.6162(2) -0.05618(13) 0.75246(19) 0.0330(5) Uani 1 1 d . . .
H9 H 0.6786 -0.0977 0.7443 0.040 Uiso 1 1 calc R U .
C10 C 0.4932(2) -0.07732(13) 0.7752(2) 0.0370(5) Uani 1 1 d . . .
H10 H 0.4711 -0.1329 0.7825 0.044 Uiso 1 1 calc R U .
C11 C 0.4017(2) -0.01760(14) 0.7874(2) 0.0344(5) Uani 1 1 d . . .
H11 H 0.3164 -0.0327 0.8025 0.041 Uiso 1 1 calc R U .
C12 C 0.4316(2) 0.06444(12) 0.77797(17) 0.0265(4) Uani 1 1 d . . .
C13 C 0.7879(2) 0.04342(14) 0.7101(2) 0.0366(5) Uani 1 1 d . . .
H13 H 0.7961 0.1036 0.7024 0.044 Uiso 1 1 calc R U .
C14 C 0.7986(3) 0.00447(19) 0.5886(3) 0.0521(7) Uani 1 1 d . . .
H14A H 0.7936 -0.0547 0.5951 0.078 Uiso 1 1 calc R U .
H14B H 0.8846 0.0196 0.5685 0.078 Uiso 1 1 calc R U .
H14C H 0.7241 0.0237 0.5247 0.078 Uiso 1 1 calc R U .
C15 C 0.9041(2) 0.01389(19) 0.8098(3) 0.0553(7) Uani 1 1 d . . .
H15A H 0.8981 0.0397 0.8867 0.083 Uiso 1 1 calc R U .
H15B H 0.9901 0.0282 0.7889 0.083 Uiso 1 1 calc R U .
H15C H 0.8985 -0.0452 0.8178 0.083 Uiso 1 1 calc R U .
C16 C 0.3251(2) 0.12720(13) 0.78947(19) 0.0296(4) Uani 1 1 d . . .
H16 H 0.3697 0.1816 0.7994 0.036 Uiso 1 1 calc R U .
C17 C 0.2128(2) 0.12979(17) 0.6742(2) 0.0414(5) Uani 1 1 d . . .
H17A H 0.2514 0.1457 0.6050 0.062 Uiso 1 1 calc R U .
H17B H 0.1441 0.1693 0.6848 0.062 Uiso 1 1 calc R U .
H17C H 0.1715 0.0760 0.6593 0.062 Uiso 1 1 calc R U .
C18 C 0.2636(2) 0.11214(17) 0.9004(2) 0.0409(5) Uani 1 1 d . . .
H18A H 0.2149 0.0604 0.8908 0.061 Uiso 1 1 calc R U .
H18B H 0.2010 0.1562 0.9079 0.061 Uiso 1 1 calc R U .
H18C H 0.3355 0.1102 0.9734 0.061 Uiso 1 1 calc R U .
C19 C -0.0755(5) 0.2500 0.4576(4) 0.0722(15) Uani 1 2 d S T P
H19A H -0.1053 0.2500 0.5356 0.087 Uiso 1 2 calc R U P
H19B H 0.0243 0.2500 0.4755 0.087 Uiso 1 2 calc R U P
C20 C 0.1684(3) 0.2500 0.2526(3) 0.0348(7) Uani 1 2 d S T P
C21 C 0.1161(5) 0.2500 0.1231(4) 0.0612(11) Uani 1 2 d S T P
H21A H 0.0332 0.2823 0.1044 0.092 Uiso 0.5 1 calc R U P
H21B H 0.0965 0.1942 0.0950 0.092 Uiso 0.5 1 calc R U P
H21C H 0.1832 0.2736 0.0822 0.092 Uiso 0.5 1 calc R U P
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 '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
C3 Re1 C1 86.74(8) . .
C3 Re1 C1 86.74(8) . 4_565
C1 Re1 C1 89.84(12) . 4_565
C3 Re1 N1 99.21(7) . .
C1 Re1 N1 97.88(7) . .
C1 Re1 N1 170.47(7) 4_565 .
C3 Re1 N1 99.21(7) . 4_565
C1 Re1 N1 170.47(7) . 4_565
C1 Re1 N1 97.88(7) 4_565 4_565
N1 Re1 N1 73.91(8) . 4_565
C3 Re1 Br1 172.90(8) . .
C1 Re1 Br1 88.24(6) . .
C1 Re1 Br1 88.24(6) 4_565 .
N1 Re1 Br1 86.44(4) . .
N1 Re1 Br1 86.44(4) 4_565 .
C4 N1 C7 118.66(15) . .
C4 N1 Re1 115.61(12) . .
C7 N1 Re1 125.73(12) . .
O1 C1 Re1 179.25(19) . .
O3 C3 Re1 173.8(2) . .
N1 C4 C4 115.50(11) . 4_565
N1 C4 C6 125.18(17) . .
C4 C4 C6 119.14(11) 4_565 .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 C12 121.77(18) . .
C8 C7 N1 121.27(17) . .
C12 C7 N1 116.96(17) . .
C9 C8 C7 117.55(19) . .
C9 C8 C13 118.72(19) . .
C7 C8 C13 123.69(18) . .
C10 C9 C8 121.8(2) . .
C10 C9 H9 119.1 . .
C8 C9 H9 119.1 . .
C9 C10 C11 119.7(2) . .
C9 C10 H10 120.1 . .
C11 C10 H10 120.1 . .
C10 C11 C12 121.4(2) . .
C10 C11 H11 119.3 . .
C12 C11 H11 119.3 . .
C11 C12 C7 117.73(19) . .
C11 C12 C16 118.84(19) . .
C7 C12 C16 123.40(18) . .
C8 C13 C15 111.2(2) . .
C8 C13 C14 110.97(19) . .
C15 C13 C14 109.7(2) . .
C8 C13 H13 108.3 . .
C15 C13 H13 108.3 . .
C14 C13 H13 108.3 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C12 C16 C18 112.26(19) . .
C12 C16 C17 111.03(17) . .
C18 C16 C17 109.85(18) . .
C12 C16 H16 107.8 . .
C18 C16 H16 107.8 . .
C17 C16 H16 107.8 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
Cl1 C19 Cl1 110.7(3) . 4_565
Cl1 C19 H19A 109.5 . .
Cl1 C19 H19A 109.5 4_565 .
Cl1 C19 H19B 109.5 . .
Cl1 C19 H19B 109.5 4_565 .
H19A C19 H19B 108.1 . .
N3 C20 C21 179.0(4) . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Re1 C3 1.904(3) .
Re1 C1 1.923(2) .
Re1 C1 1.923(2) 4_565
Re1 N1 2.1700(15) .
Re1 N1 2.1700(15) 4_565
Re1 Br1 2.6312(4) .
Cl1 C19 1.724(3) .
O1 C1 1.152(2) .
O3 C3 1.159(3) .
N1 C4 1.296(2) .
N1 C7 1.462(2) .
N3 C20 1.127(5) .
C4 C4 1.493(4) 4_565
C4 C6 1.498(3) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.400(3) .
C7 C12 1.406(3) .
C8 C9 1.399(3) .
C8 C13 1.520(3) .
C9 C10 1.371(3) .
C9 H9 0.9500 .
C10 C11 1.380(3) .
C10 H10 0.9500 .
C11 C12 1.395(3) .
C11 H11 0.9500 .
C12 C16 1.521(3) .
C13 C15 1.528(3) .
C13 C14 1.539(3) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C18 1.534(3) .
C16 C17 1.540(3) .
C16 H16 1.0000 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 Cl1 1.724(3) 4_565
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.447(5) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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_4
C7 N1 C4 C4 165.23(11) 4_565
Re1 N1 C4 C4 -14.68(13) 4_565
C7 N1 C4 C6 -9.8(3) .
Re1 N1 C4 C6 170.26(15) .
C4 N1 C7 C8 89.1(2) .
Re1 N1 C7 C8 -91.0(2) .
C4 N1 C7 C12 -90.3(2) .
Re1 N1 C7 C12 89.57(18) .
C12 C7 C8 C9 -0.6(3) .
N1 C7 C8 C9 179.94(17) .
C12 C7 C8 C13 177.15(19) .
N1 C7 C8 C13 -2.3(3) .
C7 C8 C9 C10 0.6(3) .
C13 C8 C9 C10 -177.2(2) .
C8 C9 C10 C11 -0.1(3) .
C9 C10 C11 C12 -0.5(3) .
C10 C11 C12 C7 0.5(3) .
C10 C11 C12 C16 178.6(2) .
C8 C7 C12 C11 0.1(3) .
N1 C7 C12 C11 179.54(18) .
C8 C7 C12 C16 -177.99(18) .
N1 C7 C12 C16 1.5(3) .
C9 C8 C13 C15 -63.1(3) .
C7 C8 C13 C15 119.2(2) .
C9 C8 C13 C14 59.3(3) .
C7 C8 C13 C14 -118.4(2) .
C11 C12 C16 C18 48.7(3) .
C7 C12 C16 C18 -133.2(2) .
C11 C12 C16 C17 -74.7(2) .
C7 C12 C16 C17 103.4(2) .
