#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:56:20 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179996 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/90/7029049.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_7029049
loop_
_publ_author_name
'Su, Jia-Hong'
'Lee, Gene-Hsiang'
'Peng, Shie-Ming'
'Chiu, Ching-Wen'
_publ_section_title
;
 A spiroborate-based anionic bis-N-heterocyclic carbene.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3059
_journal_page_last               3062
_journal_paper_doi               10.1039/c3dt52131a
_journal_volume                  43
_journal_year                    2014
_chemical_formula_sum            'C25 H29 Br N2 O3'
_chemical_formula_weight         485.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.7580(18)
_cell_length_b                   15.0409(14)
_cell_length_c                   17.1991(16)
_cell_measurement_reflns_used    7161
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      2.17
_cell_volume                     4852.5(8)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0721
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35835
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  0.8746
_exptl_absorpt_correction_T_min  0.4984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2001)'
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0450
_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)+(0.0585P)²+3.7123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                4057
_reflns_number_total             5580
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52131a.txt
_cod_data_source_block           ic15773
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

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_sg_symbol_H-M      Pccn
_cod_database_code               7029049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
Br1 Br 0.545744(15) 0.60057(2) 0.101588(17) 0.03687(12) Uani 1 1 d .
O1 O 0.68560(11) 0.71869(14) 0.07863(10) 0.0340(5) Uani 1 1 d .
H1 H 0.6462 0.6923 0.0835 0.051 Uiso 1 1 d R
N1 N 0.69483(12) 0.72823(15) 0.36430(12) 0.0256(5) Uani 1 1 d .
C1 C 0.7500 0.7500 0.4086(2) 0.0286(8) Uani 1 2 d S
H1A H 0.7500 0.7500 0.4639 0.034 Uiso 1 2 calc SR
C2 C 0.71508(14) 0.73554(18) 0.28640(14) 0.0235(5) Uani 1 1 d .
C3 C 0.67827(14) 0.71812(17) 0.21829(14) 0.0238(5) Uani 1 1 d .
H3 H 0.6306 0.6969 0.2187 0.029 Uiso 1 1 calc R
C4 C 0.71464(14) 0.73333(17) 0.14988(14) 0.0241(6) Uani 1 1 d .
C5 C 0.62459(14) 0.70690(19) 0.39285(14) 0.0266(6) Uani 1 1 d .
C6 C 0.61017(16) 0.6194(2) 0.41209(18) 0.0355(7) Uani 1 1 d .
C7 C 0.54200(16) 0.6012(2) 0.43964(19) 0.0395(7) Uani 1 1 d .
H7 H 0.5299 0.5417 0.4525 0.047 Uiso 1 1 calc R
C8 C 0.49130(15) 0.6673(2) 0.44883(17) 0.0343(7) Uani 1 1 d .
C9 C 0.50889(16) 0.7532(2) 0.42868(16) 0.0346(7) Uani 1 1 d .
H9 H 0.4742 0.7987 0.4343 0.042 Uiso 1 1 calc R
C10 C 0.57577(17) 0.7751(2) 0.40042(15) 0.0317(6) Uani 1 1 d .
C11 C 0.6651(2) 0.5475(2) 0.4031(2) 0.0583(11) Uani 1 1 d .
H11A H 0.6919 0.5570 0.3550 0.087 Uiso 1 1 calc R
H11B H 0.6414 0.4895 0.4011 0.087 Uiso 1 1 calc R
H11C H 0.6979 0.5491 0.4475 0.087 Uiso 1 1 calc R
C12 C 0.41753(16) 0.6461(3) 0.4791(2) 0.0462(8) Uani 1 1 d .
H12A H 0.4158 0.6573 0.5352 0.069 Uiso 1 1 calc R
H12B H 0.4066 0.5834 0.4689 0.069 Uiso 1 1 calc R
H12C H 0.3824 0.6838 0.4527 0.069 Uiso 1 1 calc R
C13 C 0.5943(2) 0.8698(2) 0.3815(2) 0.0471(8) Uani 1 1 d .
H13A H 0.6261 0.8935 0.4218 0.071 Uiso 1 1 calc R
H13B H 0.5507 0.9055 0.3795 0.071 Uiso 1 1 calc R
H13C H 0.6184 0.8722 0.3310 0.071 Uiso 1 1 calc R
O2 O 0.79074(11) 0.32042(13) 0.52555(10) 0.0321(5) Uani 1 1 d .
H2 H 0.8234 0.3584 0.5236 0.048 Uiso 1 1 d R
N2 N 0.78273(11) 0.30978(14) 0.24088(12) 0.0223(5) Uani 1 1 d .
C14 C 0.7500 0.2500 0.1957(2) 0.0227(7) Uani 1 2 d S
H14 H 0.7500 0.2500 0.1404 0.027 Uiso 1 2 calc SR
C15 C 0.77065(13) 0.28788(17) 0.31833(14) 0.0226(5) Uani 1 1 d .
C16 C 0.79335(14) 0.32848(18) 0.38662(14) 0.0252(6) Uani 1 1 d .
H16 H 0.8220 0.3805 0.3863 0.030 Uiso 1 1 calc R
C17 C 0.77173(14) 0.28862(18) 0.45498(15) 0.0257(6) Uani 1 1 d .
C18 C 0.82572(14) 0.38437(17) 0.21652(14) 0.0238(6) Uani 1 1 d .
C19 C 0.79203(15) 0.46040(18) 0.18907(16) 0.0293(6) Uani 1 1 d .
C20 C 0.83583(17) 0.53156(19) 0.17003(18) 0.0365(7) Uani 1 1 d .
H20 H 0.8150 0.5837 0.1487 0.044 Uiso 1 1 calc R
C21 C 0.90904(17) 0.5290(2) 0.18114(18) 0.0381(7) Uani 1 1 d .
C22 C 0.93936(15) 0.4521(2) 0.20950(17) 0.0346(7) Uani 1 1 d .
H22 H 0.9894 0.4502 0.2176 0.041 Uiso 1 1 calc R
C23 C 0.89896(15) 0.37720(19) 0.22661(15) 0.0275(6) Uani 1 1 d .
C24 C 0.71245(17) 0.4663(2) 0.18048(19) 0.0405(7) Uani 1 1 d .
H24A H 0.6967 0.4254 0.1396 0.061 Uiso 1 1 calc R
H24B H 0.6991 0.5272 0.1665 0.061 Uiso 1 1 calc R
H24C H 0.6897 0.4502 0.2298 0.061 Uiso 1 1 calc R
C25 C 0.9549(2) 0.6089(2) 0.1634(3) 0.0552(10) Uani 1 1 d .
H25A H 0.9552 0.6490 0.2083 0.083 Uiso 1 1 calc R
H25B H 0.9356 0.6402 0.1181 0.083 Uiso 1 1 calc R
H25C H 1.0037 0.5894 0.1522 0.083 Uiso 1 1 calc R
C26 C 0.93327(15) 0.2924(2) 0.25386(18) 0.0350(7) Uani 1 1 d .
H26A H 0.9261 0.2859 0.3100 0.052 Uiso 1 1 calc R
H26B H 0.9844 0.2942 0.2425 0.052 Uiso 1 1 calc R
H26C H 0.9116 0.2418 0.2268 0.052 Uiso 1 1 calc R
O3 O 0.89753(11) 0.43139(14) 0.50256(13) 0.0412(5) Uani 1 1 d .
H3A H 0.9088 0.4748 0.5309 0.062 Uiso 1 1 d R
H3B H 0.9340 0.4179 0.4769 0.062 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 O1 H1 109.7 . .
C1 N1 C2 108.6(2) . .
C1 N1 C5 124.9(2) . .
C2 N1 C5 126.3(2) . .
N1 C1 N1 109.8(3) . 2_665
N1 C1 H1A 125.1 . .
N1 C1 H1A 125.1 2_665 .
C2 C2 C3 122.20(15) 2_665 .
C2 C2 N1 106.43(14) 2_665 .
C3 C2 N1 131.4(2) . .
C4 C3 C2 116.3(2) . .
C4 C3 H3 121.8 . .
C2 C3 H3 121.8 . .
O1 C4 C3 123.0(2) . .
O1 C4 C4 115.61(14) . 2_665
C3 C4 C4 121.42(15) . 2_665
C10 C5 C6 123.6(3) . .
C10 C5 N1 118.2(3) . .
C6 C5 N1 118.1(3) . .
C5 C6 C7 116.7(3) . .
C5 C6 C11 121.7(3) . .
C7 C6 C11 121.6(3) . .
C8 C7 C6 121.9(3) . .
C8 C7 H7 119.0 . .
C6 C7 H7 119.0 . .
C9 C8 C7 118.7(3) . .
C9 C8 C12 120.2(3) . .
C7 C8 C12 121.1(3) . .
C8 C9 C10 121.9(3) . .
C8 C9 H9 119.1 . .
C10 C9 H9 119.1 . .
C5 C10 C9 117.2(3) . .
C5 C10 C13 122.0(3) . .
C9 C10 C13 120.7(3) . .
C6 C11 H11A 109.5 . .
C6 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C6 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C17 O2 H2 113.4 . .
C14 N2 C15 108.8(2) . .
C14 N2 C18 127.6(2) . .
C15 N2 C18 123.6(2) . .
N2 C14 N2 108.9(3) . 2_655
N2 C14 H14 125.5 . .
N2 C14 H14 125.5 2_655 .
C15 C15 C16 122.37(15) 2_655 .
C15 C15 N2 106.70(14) 2_655 .
C16 C15 N2 130.9(2) . .
C17 C16 C15 116.0(2) . .
C17 C16 H16 122.0 . .
C15 C16 H16 122.0 . .
O2 C17 C16 122.2(2) . .
O2 C17 C17 116.16(14) . 2_655
C16 C17 C17 121.61(15) . 2_655
C23 C18 C19 123.8(2) . .
C23 C18 N2 117.1(2) . .
C19 C18 N2 119.0(2) . .
C20 C19 C18 116.5(3) . .
C20 C19 C24 121.3(3) . .
C18 C19 C24 122.3(3) . .
C21 C20 C19 122.1(3) . .
C21 C20 H20 118.9 . .
C19 C20 H20 118.9 . .
C22 C21 C20 118.7(3) . .
C22 C21 C25 120.3(3) . .
C20 C21 C25 120.9(3) . .
C21 C22 C23 122.0(3) . .
C21 C22 H22 119.0 . .
C23 C22 H22 119.0 . .
C22 C23 C18 116.8(3) . .
C22 C23 C26 121.3(3) . .
C18 C23 C26 121.9(2) . .
C19 C24 H24A 109.5 . .
C19 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C19 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C21 C25 H25A 109.5 . .
C21 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C21 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C23 C26 H26A 109.5 . .
C23 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C23 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
H3A O3 H3B 106.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.359(3) .
O1 H1 0.8434 .
N1 C1 1.327(3) .
N1 C2 1.397(3) .
N1 C5 1.442(3) .
C1 N1 1.327(3) 2_665
C1 H1A 0.9500 .
C2 C2 1.380(5) 2_665
C2 C3 1.385(3) .
C3 C4 1.379(4) .
C3 H3 0.9500 .
C4 C4 1.418(5) 2_665
C5 C10 1.381(4) .
C5 C6 1.383(4) .
C6 C7 1.391(4) .
C6 C11 1.502(5) .
C7 C8 1.385(4) .
C7 H7 0.9500 .
C8 C9 1.378(4) .
C8 C12 1.513(4) .
C9 C10 1.385(4) .
C9 H9 0.9500 .
C10 C13 1.502(4) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
O2 C17 1.352(3) .
O2 H2 0.8373 .
N2 C14 1.338(3) .
N2 C15 1.391(3) .
N2 C18 1.444(3) .
C14 N2 1.338(3) 2_655
C14 H14 0.9500 .
C15 C15 1.378(5) 2_655
C15 C16 1.390(3) .
C16 C17 1.381(4) .
C16 H16 0.9500 .
C17 C17 1.419(5) 2_655
C18 C23 1.389(4) .
C18 C19 1.389(4) .
C19 C20 1.389(4) .
C19 C24 1.503(4) .
C20 C21 1.387(5) .
C20 H20 0.9500 .
C21 C22 1.379(4) .
C21 C25 1.509(4) .
C22 C23 1.389(4) .
C22 H22 0.9500 .
C23 C26 1.504(4) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
O3 H3A 0.8417 .
O3 H3B 0.8392 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Br1 0.84 2.36 3.193(2) 171.9 .
O2 H2 O3 0.84 1.81 2.637(3) 169.7 .
O3 H3A Br1 0.84 2.40 3.242(2) 172.7 8_756
O3 H3B Br1 0.84 2.51 3.342(2) 172.4 4_565
