#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/19/7001993.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_7001993
loop_
_publ_author_name
'Binobaid, Abeer'
'Iglesias, Manuel'
'Beetstra, Dirk J.'
'Kariuki, Benson'
'Dervisi, Athanasia'
'Fallis, Ian A.'
'Cavell, Kingsley J.'
_publ_section_title
;
 Expanded ring and functionalised expanded ring N-heterocyclic carbenes
 as ligands in catalysis
;
_journal_issue                   35
_journal_name_full               'Dalton Transactions'
_journal_page_first              7099
_journal_paper_doi               10.1039/b909834h
_journal_year                    2009
_chemical_formula_moiety         'C23 H31 N2 S, Br'
_chemical_formula_sum            'C23 H31 Br N2 S'
_chemical_formula_weight         447.47
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.7000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.00230(10)
_cell_length_b                   14.4043(2)
_cell_length_c                   17.6548(3)
_cell_measurement_reflns_used    3819
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.05
_cell_volume                     2268.69(6)
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXs-97
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD 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  0.2138
_diffrn_reflns_av_sigmaI/netI    0.0995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37229
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_max  0.8317
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.800
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0585
_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)+(0.0461P)²+2.3410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                3819
_reflns_number_total             5195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b909834h.txt
_cod_data_source_block           kjc0810
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7001993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.18589(5) 0.61480(3) 0.64878(2) 0.04313(16) Uani 1 1 d . . .
S2 S 0.31060(9) 0.60867(7) 0.37840(6) 0.0335(2) Uani 1 1 d . . .
C3 C 0.4857(4) 0.6247(2) 0.4343(2) 0.0249(7) Uani 1 1 d . . .
C4 C 0.6092(3) 0.6364(2) 0.39415(19) 0.0229(7) Uani 1 1 d . . .
N5 N 0.5822(3) 0.64543(18) 0.31258(15) 0.0219(6) Uani 1 1 d . . .
C6 C 0.6204(3) 0.5779(2) 0.26808(18) 0.0208(6) Uani 1 1 d . . .
H6 H 0.6680 0.5244 0.2917 0.025 Uiso 1 1 calc R . .
N7 N 0.5960(3) 0.58082(17) 0.19325(15) 0.0204(5) Uani 1 1 d . . .
C8 C 0.6570(3) 0.5100(2) 0.14825(17) 0.0216(6) Uani 1 1 d . . .
C9 C 0.8041(3) 0.5216(2) 0.13136(18) 0.0247(7) Uani 1 1 d . . .
C10 C 0.8570(4) 0.4539(2) 0.08497(19) 0.0283(7) Uani 1 1 d . . .
H10 H 0.9555 0.4593 0.0718 0.034 Uiso 1 1 calc R . .
C11 C 0.7702(4) 0.3800(2) 0.0581(2) 0.0321(8) Uani 1 1 d . . .
H11 H 0.8091 0.3352 0.0265 0.038 Uiso 1 1 calc R . .
C12 C 0.6265(4) 0.3696(2) 0.0764(2) 0.0307(8) Uani 1 1 d . . .
H12 H 0.5682 0.3175 0.0575 0.037 Uiso 1 1 calc R . .
C13 C 0.5662(4) 0.4347(2) 0.12213(19) 0.0260(7) Uani 1 1 d . . .
C14 C 0.4122(4) 0.4205(3) 0.1464(2) 0.0334(8) Uani 1 1 d . . .
H14 H 0.3787 0.4813 0.1656 0.040 Uiso 1 1 calc R . .
C15 C 0.2959(4) 0.3898(3) 0.0801(3) 0.0477(11) Uani 1 1 d . . .
H15A H 0.2909 0.4356 0.0388 0.072 Uiso 1 1 calc R . .
H15B H 0.1975 0.3847 0.0978 0.072 Uiso 1 1 calc R . .
H15C H 0.3246 0.3293 0.0612 0.072 Uiso 1 1 calc R . .
C17 C 0.4201(5) 0.3507(4) 0.2119(3) 0.0617(13) Uani 1 1 d . . .
H17A H 0.4504 0.2900 0.1943 0.093 Uiso 1 1 calc R . .
H17B H 0.3214 0.3456 0.2292 0.093 Uiso 1 1 calc R . .
H17C H 0.4936 0.3719 0.2544 0.093 Uiso 1 1 calc R . .
C18 C 0.9029(4) 0.6007(2) 0.1631(2) 0.0322(8) Uani 1 1 d . . .
H18 H 0.8378 0.6469 0.1853 0.039 Uiso 1 1 calc R . .
C19 C 1.0194(5) 0.5665(3) 0.2281(3) 0.0554(12) Uani 1 1 d . . .
H19A H 0.9686 0.5359 0.2670 0.083 Uiso 1 1 calc R . .
H19B H 1.0774 0.6194 0.2511 0.083 Uiso 1 1 calc R . .
H19C H 1.0870 0.5223 0.2079 0.083 Uiso 1 1 calc R . .
C20 C 0.9791(5) 0.6505(3) 0.1039(3) 0.0546(12) Uani 1 1 d . . .
H20A H 1.0465 0.6074 0.0822 0.082 Uiso 1 1 calc R . .
H20B H 1.0370 0.7029 0.1277 0.082 Uiso 1 1 calc R . .
H20C H 0.9034 0.6734 0.0631 0.082 Uiso 1 1 calc R . .
C21 C 0.5165(3) 0.6591(2) 0.15131(18) 0.0249(7) Uani 1 1 d . . .
H21A H 0.4505 0.6351 0.1062 0.030 Uiso 1 1 calc R . .
H21B H 0.5902 0.7018 0.1331 0.030 Uiso 1 1 calc R . .
C22 C 0.4235(3) 0.7112(2) 0.2026(2) 0.0277(7) Uani 1 1 d . . .
H22A H 0.3358 0.6732 0.2113 0.033 Uiso 1 1 calc R . .
H22B H 0.3863 0.7697 0.1774 0.033 Uiso 1 1 calc R . .
C23 C 0.5169(4) 0.7328(2) 0.27822(19) 0.0255(7) Uani 1 1 d . . .
H23A H 0.5980 0.7766 0.2703 0.031 Uiso 1 1 calc R . .
H23B H 0.4534 0.7622 0.3131 0.031 Uiso 1 1 calc R . .
C24 C 0.7535(4) 0.6408(2) 0.4319(2) 0.0284(7) Uani 1 1 d . . .
H24 H 0.8354 0.6472 0.4036 0.034 Uiso 1 1 calc R . .
C25 C 0.7797(4) 0.6359(2) 0.5112(2) 0.0326(8) Uani 1 1 d . . .
H25 H 0.8790 0.6381 0.5373 0.039 Uiso 1 1 calc R . .
C26 C 0.6580(4) 0.6277(2) 0.5514(2) 0.0314(8) Uani 1 1 d . . .
H26 H 0.6744 0.6263 0.6057 0.038 Uiso 1 1 calc R . .
C27 C 0.5129(4) 0.6214(2) 0.5137(2) 0.0298(8) Uani 1 1 d . . .
H27 H 0.4314 0.6147 0.5424 0.036 Uiso 1 1 calc R . .
C28 C 0.1814(4) 0.6006(3) 0.4478(2) 0.0408(9) Uani 1 1 d . . .
H28A H 0.2197 0.5561 0.4876 0.061 Uiso 1 1 calc R . .
H28B H 0.0836 0.5797 0.4225 0.061 Uiso 1 1 calc R . .
H28C H 0.1708 0.6617 0.4709 0.061 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'
S S 0.1246 0.1234 '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
C3 S2 C28 103.81(18) . . ?
C27 C3 C4 117.9(3) . . ?
C27 C3 S2 125.7(3) . . ?
C4 C3 S2 116.3(3) . . ?
C24 C4 C3 121.2(3) . . ?
C24 C4 N5 120.2(3) . . ?
C3 C4 N5 118.6(3) . . ?
C6 N5 C4 120.4(3) . . ?
C6 N5 C23 120.0(3) . . ?
C4 N5 C23 119.5(2) . . ?
N7 C6 N5 123.5(3) . . ?
C6 N7 C8 120.4(3) . . ?
C6 N7 C21 122.2(3) . . ?
C8 N7 C21 117.2(2) . . ?
C13 C8 C9 123.2(3) . . ?
C13 C8 N7 118.7(3) . . ?
C9 C8 N7 118.1(3) . . ?
C10 C9 C8 116.5(3) . . ?
C10 C9 C18 121.0(3) . . ?
C8 C9 C18 122.5(3) . . ?
C11 C10 C9 121.5(3) . . ?
C10 C11 C12 120.8(3) . . ?
C11 C12 C13 120.8(3) . . ?
C12 C13 C8 117.1(3) . . ?
C12 C13 C14 121.0(3) . . ?
C8 C13 C14 121.8(3) . . ?
C13 C14 C17 110.5(3) . . ?
C13 C14 C15 112.3(3) . . ?
C17 C14 C15 110.3(3) . . ?
C9 C18 C20 113.7(3) . . ?
C9 C18 C19 110.3(3) . . ?
C20 C18 C19 110.1(3) . . ?
N7 C21 C22 110.4(3) . . ?
C21 C22 C23 110.1(3) . . ?
N5 C23 C22 109.3(3) . . ?
C4 C24 C25 120.4(3) . . ?
C26 C25 C24 118.7(3) . . ?
C27 C26 C25 121.2(3) . . ?
C26 C27 C3 120.5(3) . . ?
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
S2 C3 1.759(3) . ?
S2 C28 1.802(4) . ?
C3 C27 1.393(5) . ?
C3 C4 1.406(5) . ?
C4 C24 1.380(5) . ?
C4 N5 1.434(4) . ?
N5 C6 1.325(4) . ?
N5 C23 1.484(4) . ?
C6 N7 1.310(4) . ?
N7 C8 1.446(4) . ?
N7 C21 1.480(4) . ?
C8 C13 1.399(4) . ?
C8 C9 1.405(4) . ?
C9 C10 1.398(5) . ?
C9 C18 1.507(5) . ?
C10 C11 1.367(5) . ?
C11 C12 1.383(5) . ?
C12 C13 1.394(5) . ?
C13 C14 1.519(4) . ?
C14 C17 1.527(6) . ?
C14 C15 1.528(5) . ?
C18 C20 1.507(5) . ?
C18 C19 1.528(5) . ?
C21 C22 1.512(4) . ?
C22 C23 1.512(5) . ?
C24 C25 1.389(5) . ?
C25 C26 1.389(5) . ?
C26 C27 1.387(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652616
