#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:22:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178561 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/69/4066989.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_4066989
loop_
_publ_author_name
'Yang, Chien-Chan'
'Lin, Pei-Syuan'
'Liu, Fu-Chen'
'Lin, Ivan J. B.'
'Lee, Gene-Hsian'
'Peng, Shie-Ming'
_publ_section_title
;
 Glucopyranoside-Incorporated N-Heterocyclic Carbene Complexes of
 Silver(I) and Palladium(II): Efficient Water-Soluble
 Suzuki−Miyaura Coupling Palladium(II) Catalysts
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              5959
_journal_paper_doi               10.1021/om100751r
_journal_volume                  29
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H35 Br N2 O9'
_chemical_formula_weight         683.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 90.400(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   42.873(7)
_cell_length_b                   5.7060(10)
_cell_length_c                   13.107(2)
_cell_measurement_reflns_used    2498
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.87
_cell_measurement_theta_min      2.45
_cell_volume                     3206.3(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16123
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         0.95
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.825
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         7341
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+1.6901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                5692
_reflns_number_total             7341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100751r_si_001.cif
_cod_data_source_block           ic12626
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3206.2(10)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4066989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 0.0000 -0.53547(13) -0.5000 0.0654(3) Uani 1 2 d S . .
Br2 Br 0.03202(2) 0.33197(18) 0.06686(6) 0.0452(3) Uani 0.50 1 d P . .
O1 O 0.08666(6) 0.0448(5) -0.3230(2) 0.0274(6) Uani 1 1 d . . .
O2 O 0.10178(6) -0.3396(5) -0.3557(2) 0.0284(6) Uani 1 1 d . . .
O3 O 0.16282(6) -0.2263(5) -0.37083(18) 0.0258(6) Uani 1 1 d . . .
O4 O 0.15477(7) -0.1307(5) -0.53538(19) 0.0339(7) Uani 1 1 d . . .
O5 O 0.17539(6) 0.0496(5) -0.20205(19) 0.0255(6) Uani 1 1 d . . .
O6 O 0.18642(8) -0.2925(6) -0.1237(3) 0.0545(10) Uani 1 1 d . . .
O7 O 0.12405(7) 0.1324(5) -0.0739(2) 0.0286(6) Uani 1 1 d . . .
O8 O 0.11106(7) 0.5166(5) -0.0645(2) 0.0387(7) Uani 1 1 d . . .
N1 N 0.03205(9) 0.0536(8) -0.2050(3) 0.0429(10) Uani 1 1 d . . .
N2 N -0.00902(9) -0.0451(9) -0.2918(4) 0.0554(12) Uani 1 1 d . B .
C1 C 0.10746(9) -0.1050(6) -0.3735(3) 0.0247(8) Uani 1 1 d . . .
H1 H 0.1055 -0.0759 -0.4485 0.030 Uiso 1 1 calc R . .
C2 C 0.14097(8) -0.0477(7) -0.3403(3) 0.0245(7) Uani 1 1 d . . .
H2 H 0.1473 0.1055 -0.3710 0.029 Uiso 1 1 calc R . .
C3 C 0.14436(8) -0.0332(7) -0.2248(3) 0.0240(7) Uani 1 1 d . . .
H3 H 0.1414 -0.1923 -0.1944 0.029 Uiso 1 1 calc R . .
C4 C 0.12024(9) 0.1335(7) -0.1825(3) 0.0245(8) Uani 1 1 d . . .
H4 H 0.1233 0.2949 -0.2104 0.029 Uiso 1 1 calc R . .
C5 C 0.08855(9) 0.0363(7) -0.2144(3) 0.0279(8) Uani 1 1 d . . .
H5 H 0.0867 -0.1298 -0.1910 0.034 Uiso 1 1 calc R . .
C6 C 0.07411(10) -0.4133(8) -0.4081(4) 0.0413(11) Uani 1 1 d . . .
H6A H 0.0559 -0.3420 -0.3759 0.062 Uiso 1 1 calc R . .
H6B H 0.0724 -0.5844 -0.4047 0.062 Uiso 1 1 calc R . .
H6C H 0.0751 -0.3641 -0.4796 0.062 Uiso 1 1 calc R . .
C7 C 0.16726(8) -0.2524(7) -0.4720(3) 0.0242(8) Uani 1 1 d . . .
C8 C 0.18861(9) -0.4489(7) -0.4938(3) 0.0251(8) Uani 1 1 d . . .
C9 C 0.20017(9) -0.4727(7) -0.5929(3) 0.0282(8) Uani 1 1 d . . .
H9 H 0.1951 -0.3589 -0.6432 0.034 Uiso 1 1 calc R . .
C10 C 0.21884(9) -0.6608(8) -0.6176(3) 0.0308(8) Uani 1 1 d . . .
H10 H 0.2267 -0.6764 -0.6849 0.037 Uiso 1 1 calc R . .
C11 C 0.22608(9) -0.8260(7) -0.5446(3) 0.0308(9) Uani 1 1 d . . .
H11 H 0.2386 -0.9570 -0.5620 0.037 Uiso 1 1 calc R . .
C12 C 0.21503(9) -0.8021(7) -0.4445(3) 0.0301(9) Uani 1 1 d . . .
H12 H 0.2204 -0.9153 -0.3942 0.036 Uiso 1 1 calc R . .
C13 C 0.19644(9) -0.6154(7) -0.4194(3) 0.0251(8) Uani 1 1 d . . .
H13 H 0.1889 -0.5990 -0.3517 0.030 Uiso 1 1 calc R . .
C14 C 0.19451(10) -0.1037(7) -0.1526(3) 0.0288(9) Uani 1 1 d . . .
C15 C 0.22721(8) -0.0145(7) -0.1425(3) 0.0245(8) Uani 1 1 d . . .
C16 C 0.24870(9) -0.1632(8) -0.0975(3) 0.0277(8) Uani 1 1 d . . .
H16 H 0.2421 -0.3102 -0.0714 0.033 Uiso 1 1 calc R . .
C17 C 0.28007(9) -0.0990(7) -0.0901(3) 0.0292(9) Uani 1 1 d . . .
H17 H 0.2949 -0.2019 -0.0595 0.035 Uiso 1 1 calc R . .
C18 C 0.28944(9) 0.1185(8) -0.1282(3) 0.0303(9) Uani 1 1 d . . .
H18 H 0.3107 0.1639 -0.1240 0.036 Uiso 1 1 calc R . .
C19 C 0.26780(9) 0.2671(7) -0.1719(3) 0.0310(9) Uani 1 1 d . . .
H19 H 0.2743 0.4148 -0.1976 0.037 Uiso 1 1 calc R . .
C20 C 0.23682(9) 0.2039(7) -0.1789(3) 0.0277(8) Uani 1 1 d . . .
H20 H 0.2221 0.3084 -0.2084 0.033 Uiso 1 1 calc R . .
C21 C 0.11978(9) 0.3378(7) -0.0229(3) 0.0281(8) Uani 1 1 d . . .
C22 C 0.12715(9) 0.3117(7) 0.0870(3) 0.0278(8) Uani 1 1 d . . .
C23 C 0.14131(10) 0.1101(8) 0.1255(3) 0.0338(9) Uani 1 1 d . . .
H23 H 0.1465 -0.0155 0.0812 0.041 Uiso 1 1 calc R . .
C24 C 0.14779(10) 0.0946(9) 0.2289(3) 0.0384(10) Uani 1 1 d . . .
H24 H 0.1581 -0.0402 0.2549 0.046 Uiso 1 1 calc R . .
C25 C 0.13947(11) 0.2710(9) 0.2941(3) 0.0394(11) Uani 1 1 d . . .
H25 H 0.1432 0.2550 0.3653 0.047 Uiso 1 1 calc R . .
C26 C 0.12573(12) 0.4719(10) 0.2564(4) 0.0478(12) Uani 1 1 d . . .
H26 H 0.1206 0.5959 0.3016 0.057 Uiso 1 1 calc R . .
C27 C 0.11931(11) 0.4944(8) 0.1526(3) 0.0395(10) Uani 1 1 d . . .
H27 H 0.1097 0.6325 0.1269 0.047 Uiso 1 1 calc R . .
C28 C 0.06094(10) 0.1757(9) -0.1768(4) 0.0388(10) Uani 1 1 d . . .
H28A H 0.0622 0.1933 -0.1018 0.047 Uiso 1 1 calc R . .
H28B H 0.0611 0.3340 -0.2077 0.047 Uiso 1 1 calc R . .
C29 C 0.01350(10) 0.1115(10) -0.2833(4) 0.0472(12) Uani 1 1 d . . .
H29 H 0.0161 0.2443 -0.3261 0.057 Uiso 1 1 calc R . .
C30 C 0.02095(13) -0.1496(12) -0.1630(4) 0.0600(15) Uani 1 1 d . . .
H30 H 0.0297 -0.2319 -0.1067 0.072 Uiso 1 1 calc R . .
C31 C -0.00482(13) -0.2108(13) -0.2169(6) 0.0715(19) Uani 1 1 d . . .
H31 H -0.0176 -0.3438 -0.2052 0.086 Uiso 1 1 calc R . .
C32 C -0.03489(11) -0.0436(13) -0.3646(5) 0.0691(18) Uani 1 1 d D . .
H32A H -0.0349 -0.1904 -0.4049 0.083 Uiso 0.50 1 calc PR A 1
H32B H -0.0327 0.0900 -0.4122 0.083 Uiso 0.50 1 calc PR A 1
H32C H -0.0345 -0.1883 -0.4063 0.083 Uiso 0.50 1 d PR A 2
H32D H -0.0332 0.0929 -0.4109 0.083 Uiso 0.50 1 d PR A 2
C33 C -0.0653(2) -0.022(2) -0.3058(8) 0.062(3) Uiso 0.55 1 d PD B 1
H33A H -0.0699 -0.1704 -0.2716 0.092 Uiso 0.50 1 calc PR B 1
H33B H -0.0824 0.0168 -0.3532 0.092 Uiso 0.50 1 calc PR B 1
H33C H -0.0633 0.1030 -0.2547 0.092 Uiso 0.50 1 calc PR B 1
C33' C -0.0640(3) 0.104(3) -0.3290(10) 0.059(3) Uiso 0.45 1 d PD B 2
H33D H -0.0628 0.2624 -0.3577 0.089 Uiso 0.50 1 calc PR B 2
H33E H -0.0641 0.1138 -0.2543 0.089 Uiso 0.50 1 calc PR B 2
H33F H -0.0832 0.0280 -0.3527 0.089 Uiso 0.50 1 calc PR B 2
O9 O 0.06189(15) 0.8187(18) 0.0398(5) 0.164(4) Uani 1 1 d . . .
H9A H 0.0588 0.9421 0.0725 0.247 Uiso 1 1 d R . .
H9B H 0.0770 0.8259 0.0022 0.247 Uiso 1 1 d 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C5 114.7(3)
C1 O2 C6 110.5(3)
C7 O3 C2 116.5(3)
C14 O5 C3 116.1(3)
C21 O7 C4 118.0(3)
C29 N1 C30 108.1(5)
C29 N1 C28 125.0(4)
C30 N1 C28 126.6(5)
C29 N2 C31 108.3(5)
C29 N2 C32 127.1(6)
C31 N2 C32 124.6(5)
O2 C1 O1 113.4(3)
O2 C1 C2 109.0(3)
O1 C1 C2 109.5(3)
O3 C2 C3 104.8(3)
O3 C2 C1 112.3(3)
C3 C2 C1 112.1(3)
O5 C3 C4 110.5(3)
O5 C3 C2 107.7(3)
C4 C3 C2 109.7(3)
O7 C4 C3 106.7(3)
O7 C4 C5 111.5(3)
C3 C4 C5 106.4(3)
O1 C5 C28 105.6(3)
O1 C5 C4 107.8(3)
C28 C5 C4 114.7(3)
O4 C7 O3 123.3(4)
O4 C7 C8 125.2(3)
O3 C7 C8 111.5(3)
C9 C8 C13 119.7(4)
C9 C8 C7 118.5(3)
C13 C8 C7 121.7(3)
C10 C9 C8 120.3(4)
C11 C10 C9 119.8(3)
C10 C11 C12 120.5(4)
C13 C12 C11 120.0(4)
C12 C13 C8 119.8(3)
O6 C14 O5 123.8(4)
O6 C14 C15 123.5(4)
O5 C14 C15 112.6(3)
C16 C15 C20 119.7(4)
C16 C15 C14 116.8(3)
C20 C15 C14 123.5(3)
C15 C16 C17 120.5(4)
C16 C17 C18 119.1(4)
C19 C18 C17 120.0(4)
C18 C19 C20 120.8(4)
C19 C20 C15 119.8(4)
O8 C21 O7 123.0(3)
O8 C21 C22 125.7(4)
O7 C21 C22 111.3(3)
C27 C22 C23 120.0(4)
C27 C22 C21 118.4(4)
C23 C22 C21 121.7(4)
C24 C23 C22 119.5(4)
C25 C24 C23 120.8(5)
C24 C25 C26 120.0(4)
C25 C26 C27 120.5(4)
C26 C27 C22 119.2(4)
N1 C28 C5 109.3(4)
N2 C29 N1 109.2(5)
C31 C30 N1 107.0(6)
C30 C31 N2 107.3(6)
N2 C32 C33 108.6(6)
N2 C32 C33' 114.1(6)
C33 C32 C33' 29.1(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.404(4)
O1 C5 1.426(5)
O2 C1 1.381(5)
O2 C6 1.430(5)
O3 C7 1.349(4)
O3 C2 1.443(5)
O4 C7 1.205(4)
O5 C14 1.360(5)
O5 C3 1.441(4)
O6 C14 1.194(5)
O7 C21 1.362(5)
O7 C4 1.431(4)
O8 C21 1.214(5)
N1 C29 1.335(7)
N1 C30 1.370(8)
N1 C28 1.466(6)
N2 C29 1.320(7)
N2 C31 1.373(9)
N2 C32 1.458(7)
C1 C2 1.534(5)
C2 C3 1.523(5)
C3 C4 1.513(5)
C4 C5 1.523(5)
C5 C28 1.511(6)
C7 C8 1.477(6)
C8 C9 1.400(5)
C8 C13 1.401(5)
C9 C10 1.379(6)
C10 C11 1.378(6)
C11 C12 1.404(6)
C12 C13 1.372(6)
C14 C15 1.497(5)
C15 C16 1.382(5)
C15 C20 1.397(6)
C16 C17 1.397(6)
C17 C18 1.398(6)
C18 C19 1.378(6)
C19 C20 1.379(6)
C21 C22 1.481(5)
C22 C27 1.394(6)
C22 C23 1.394(6)
C23 C24 1.383(6)
C24 C25 1.370(7)
C25 C26 1.379(7)
C26 C27 1.391(7)
C30 C31 1.353(8)
C32 C33 1.526(10)
C32 C33' 1.580(12)
