#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:09:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180170 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/66/7106682.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_7106682
loop_
_publ_author_name
'Yunshan Sun'
'Christian Koehler'
'Runyu Tan'
'Vincent T. Annibale'
'Datong Song'
_publ_section_title
;
 Ester hydrogenation catalyzed by Ru-CNN pincer complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              8349
_journal_paper_doi               10.1039/c1cc12601f
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C23 H31 Br N4'
_chemical_formula_weight         443.43
_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                 108.4310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9717(2)
_cell_length_b                   27.7991(8)
_cell_length_c                   9.8235(2)
_cell_measurement_reflns_used    17718
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.30
_cell_volume                     2324.36(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17718
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Apex 2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.0875
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0302P)²+1.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                3402
_reflns_number_total             4087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12601f.txt
_cod_data_source_block           1bHBr
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7106682
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84089(2) 0.052738(9) 0.21893(2) 0.02624(8) Uani 1 1 d . . .
N1 N 1.0619(3) 0.26239(8) -0.2832(2) 0.0501(6) Uani 1 1 d . . .
N2 N 1.0391(2) 0.14131(7) -0.13813(19) 0.0277(4) Uani 1 1 d . . .
N3 N 1.1813(2) 0.05873(7) 0.04860(18) 0.0213(4) Uani 1 1 d . . .
N4 N 1.35356(19) 0.07114(7) 0.25571(18) 0.0210(4) Uani 1 1 d . . .
C1 C 0.7813(4) 0.28524(14) -0.3833(4) 0.0741(11) Uani 1 1 d . . .
H1A H 0.7096 0.3128 -0.3997 0.111 Uiso 1 1 calc R A .
H1B H 0.7507 0.2614 -0.3235 0.111 Uiso 1 1 calc R . .
H1C H 0.7759 0.2707 -0.4756 0.111 Uiso 1 1 calc R . .
C2 C 0.9472(4) 0.30199(10) -0.3079(3) 0.0589(9) Uani 1 1 d . . .
H2A H 0.9757 0.3271 -0.3666 0.071 Uiso 1 1 calc R . .
H2B H 0.9521 0.3165 -0.2146 0.071 Uiso 1 1 calc R . .
C3 C 1.3307(9) 0.2426(3) -0.2085(9) 0.072(2) Uiso 0.50 1 d P A 1
H3A H 1.4347 0.2572 -0.1670 0.107 Uiso 0.50 1 calc PR A 1
H3B H 1.3224 0.2288 -0.3024 0.107 Uiso 0.50 1 calc PR A 1
H3C H 1.3163 0.2172 -0.1447 0.107 Uiso 0.50 1 calc PR A 1
C3A C 1.3485(8) 0.2400(3) -0.2718(8) 0.0588(18) Uiso 0.50 1 d P B 2
H3AA H 1.4534 0.2535 -0.2564 0.088 Uiso 0.50 1 calc PR B 2
H3AB H 1.3103 0.2255 -0.3675 0.088 Uiso 0.50 1 calc PR B 2
H3AC H 1.3535 0.2154 -0.1991 0.088 Uiso 0.50 1 calc PR B 2
C4 C 1.2008(9) 0.2821(3) -0.2268(9) 0.066(2) Uiso 0.50 1 d P A 1
H4A H 1.2089 0.2962 -0.1322 0.079 Uiso 0.50 1 calc PR A 1
H4B H 1.2158 0.3081 -0.2900 0.079 Uiso 0.50 1 calc PR A 1
C4A C 1.2386(8) 0.2792(3) -0.2603(8) 0.0486(17) Uiso 0.50 1 d P B 2
H4AA H 1.2372 0.3043 -0.3323 0.058 Uiso 0.50 1 calc PR B 2
H4AB H 1.2804 0.2942 -0.1642 0.058 Uiso 0.50 1 calc PR B 2
C5 C 1.0403(4) 0.22675(10) -0.1818(3) 0.0558(9) Uani 1 1 d . A .
H5A H 0.9413 0.2339 -0.1613 0.067 Uiso 1 1 calc R . .
H5B H 1.1277 0.2297 -0.0906 0.067 Uiso 1 1 calc R . .
C6 C 1.0343(3) 0.17559(9) -0.2350(2) 0.0301(5) Uani 1 1 d . . .
C7 C 1.0191(3) 0.16506(9) -0.3773(2) 0.0300(5) Uani 1 1 d . A .
H7A H 1.0141 0.1902 -0.4441 0.036 Uiso 1 1 calc R . .
C8 C 1.0114(3) 0.11779(9) -0.4198(2) 0.0292(5) Uani 1 1 d . . .
H8A H 1.0013 0.1098 -0.5163 0.035 Uiso 1 1 calc R A .
C9 C 1.0187(2) 0.08202(8) -0.3202(2) 0.0253(5) Uani 1 1 d . A .
H9A H 1.0158 0.0490 -0.3462 0.030 Uiso 1 1 calc R . .
C10 C 1.0303(2) 0.09554(8) -0.1818(2) 0.0208(5) Uani 1 1 d . . .
C11 C 1.0320(2) 0.05808(8) -0.0705(2) 0.0227(5) Uani 1 1 d . A .
H11A H 0.9439 0.0641 -0.0323 0.027 Uiso 1 1 calc R . .
H11B H 1.0164 0.0259 -0.1158 0.027 Uiso 1 1 calc R . .
C12 C 1.3240(3) 0.04280(9) 0.0408(2) 0.0292(6) Uani 1 1 d . . .
H12A H 1.3428 0.0290 -0.0407 0.035 Uiso 1 1 calc R . .
C13 C 1.4315(3) 0.05046(9) 0.1696(2) 0.0289(5) Uani 1 1 d . . .
H13A H 1.5403 0.0431 0.1963 0.035 Uiso 1 1 calc R . .
C14 C 1.2026(2) 0.07591(8) 0.1787(2) 0.0205(5) Uani 1 1 d . . .
H14A H 1.1233 0.0895 0.2120 0.025 Uiso 1 1 calc R . .
C15 C 1.4194(2) 0.08223(8) 0.4072(2) 0.0233(5) Uani 1 1 d . . .
C16 C 1.5303(2) 0.11883(9) 0.4491(2) 0.0277(5) Uani 1 1 d . . .
C17 C 1.5889(3) 0.12867(10) 0.5956(3) 0.0362(6) Uani 1 1 d . . .
H17A H 1.6654 0.1533 0.6279 0.043 Uiso 1 1 calc R . .
C18 C 1.5397(3) 0.10379(11) 0.6957(3) 0.0387(6) Uani 1 1 d . . .
C19 C 1.4312(3) 0.06706(10) 0.6479(2) 0.0342(6) Uani 1 1 d . . .
H19A H 1.3978 0.0496 0.7161 0.041 Uiso 1 1 calc R . .
C20 C 1.3697(2) 0.05494(9) 0.5038(2) 0.0271(5) Uani 1 1 d . . .
C21 C 1.5888(3) 0.14616(9) 0.3437(3) 0.0354(6) Uani 1 1 d . . .
H21A H 1.6399 0.1759 0.3884 0.053 Uiso 1 1 calc R . .
H21B H 1.5000 0.1540 0.2585 0.053 Uiso 1 1 calc R . .
H21C H 1.6645 0.1263 0.3155 0.053 Uiso 1 1 calc R . .
C22 C 1.6022(3) 0.11634(14) 0.8534(3) 0.0599(9) Uani 1 1 d . . .
H22A H 1.6322 0.0868 0.9099 0.090 Uiso 1 1 calc R . .
H22B H 1.5206 0.1331 0.8818 0.090 Uiso 1 1 calc R . .
H22C H 1.6943 0.1372 0.8707 0.090 Uiso 1 1 calc R . .
C23 C 1.2572(3) 0.01363(9) 0.4565(2) 0.0321(6) Uani 1 1 d . . .
H23A H 1.2913 -0.0071 0.3912 0.048 Uiso 1 1 calc R . .
H23B H 1.1517 0.0260 0.4068 0.048 Uiso 1 1 calc R . .
H23C H 1.2551 -0.0050 0.5405 0.048 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C4 N1 C5 107.9(4) . . ?
C4 N1 C2 106.1(4) . . ?
C5 N1 C2 112.5(2) . . ?
C5 N1 C4A 116.2(3) . . ?
C2 N1 C4A 114.4(3) . . ?
C10 N2 C6 117.68(18) . . ?
C14 N3 C12 108.49(18) . . ?
C14 N3 C11 126.12(18) . . ?
C12 N3 C11 125.37(18) . . ?
C14 N4 C13 108.30(18) . . ?
C14 N4 C15 124.93(17) . . ?
C13 N4 C15 126.58(17) . . ?
N1 C2 C1 112.2(3) . . ?
N1 C4 C3 109.2(6) . . ?
C3A C4A N1 115.0(5) . . ?
N1 C5 C6 113.6(2) . . ?
N2 C6 C7 122.4(2) . . ?
N2 C6 C5 115.8(2) . . ?
C7 C6 C5 121.8(2) . . ?
C8 C7 C6 119.0(2) . . ?
C7 C8 C9 119.1(2) . . ?
C8 C9 C10 118.2(2) . . ?
N2 C10 C9 123.6(2) . . ?
N2 C10 C11 116.02(18) . . ?
C9 C10 C11 120.4(2) . . ?
N3 C11 C10 111.42(17) . . ?
C13 C12 N3 107.4(2) . . ?
C12 C13 N4 106.94(19) . . ?
N3 C14 N4 108.86(18) . . ?
C16 C15 C20 123.4(2) . . ?
C16 C15 N4 118.69(19) . . ?
C20 C15 N4 117.95(19) . . ?
C15 C16 C17 116.7(2) . . ?
C15 C16 C21 122.5(2) . . ?
C17 C16 C21 120.7(2) . . ?
C18 C17 C16 122.3(2) . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 C22 121.0(3) . . ?
C19 C18 C22 120.7(3) . . ?
C18 C19 C20 122.3(2) . . ?
C19 C20 C15 116.9(2) . . ?
C19 C20 C23 120.8(2) . . ?
C15 C20 C23 122.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.313(8) . ?
N1 C5 1.461(3) . ?
N1 C2 1.473(4) . ?
N1 C4A 1.599(7) . ?
N2 C10 1.337(3) . ?
N2 C6 1.338(3) . ?
N3 C14 1.321(3) . ?
N3 C12 1.380(3) . ?
N3 C11 1.474(3) . ?
N4 C14 1.333(3) . ?
N4 C13 1.381(3) . ?
N4 C15 1.450(3) . ?
C1 C2 1.512(5) . ?
C3 C4 1.569(11) . ?
C3A C4A 1.498(10) . ?
C5 C6 1.510(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.374(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.507(3) . ?
C12 C13 1.343(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.394(3) . ?
C16 C17 1.395(3) . ?
C16 C21 1.506(3) . ?
C17 C18 1.383(4) . ?
C18 C19 1.386(4) . ?
C18 C22 1.512(3) . ?
C19 C20 1.388(3) . ?
C20 C23 1.503(3) . ?
