#------------------------------------------------------------------------------
#$Date: 2019-11-23 15:12:57 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/59/7235948.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_7235948
loop_
_publ_author_name
'Gupta, Vivek'
'Karthik, Vedhagiri'
'Anantharaman, Ganapathi'
_publ_section_title
;
 Labile dioxy-functionalised zwitterionic imidazolinium salt: access to
 zwitterionic and neutral imidazolidin-2-ylidene derivatives and
 π-acceptor properties of imidazolidine-2-selones
;
_journal_issue                   107
_journal_name_full               'RSC Advances'
_journal_page_first              87888
_journal_paper_doi               10.1039/C5RA15333F
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C21 H25 B F2 N2 O2'
_chemical_formula_sum            'C21 H25 B F2 N2 O2'
_chemical_formula_weight         386.24
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.3720(18)
_cell_length_b                   10.6579(9)
_cell_length_c                   8.0526(7)
_cell_measurement_reflns_used    2910
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      3.30
_cell_volume                     1920.1(3)
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'diamond 3.1d'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6800
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.7935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0701
_reflns_number_gt                1636
_reflns_number_total             1824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra15333f2.cif
_cod_data_source_block           2apra
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_hydrogen_treatment' value 'Constr' was changed
to 'constr' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Cmc2(1)
_cod_database_code               7235948
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-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
B1 B 0.0000 0.2183(3) 0.4181(4) 0.0215(6) Uani 1 2 d S
C1 C 0.0000 0.1868(2) 0.8651(3) 0.0128(5) Uani 1 2 d S
H1 H 0.0000 0.1315 0.9544 0.015 Uiso 1 2 calc SR
C2 C 0.03466(7) 0.31649(16) 0.6569(2) 0.0167(4) Uani 1 1 d .
H2 H 0.0505 0.4008 0.6781 0.020 Uiso 1 1 calc R
C4 C 0.11026(7) 0.20768(15) 0.8477(2) 0.0135(4) Uani 1 1 d .
C5 C 0.13708(7) 0.29638(14) 0.9502(2) 0.0161(4) Uani 1 1 d .
C6 C 0.19732(7) 0.28208(16) 0.9851(2) 0.0189(4) Uani 1 1 d .
H6 H 0.2161 0.3411 1.0523 0.023 Uiso 1 1 calc R
C7 C 0.23061(7) 0.18280(16) 0.9231(2) 0.0192(4) Uani 1 1 d .
C8 C 0.20143(7) 0.09414(16) 0.8265(2) 0.0169(4) Uani 1 1 d .
H8 H 0.2229 0.0252 0.7881 0.020 Uiso 1 1 calc R
C9 C 0.14116(7) 0.10456(15) 0.7849(2) 0.0142(4) Uani 1 1 d .
C10 C 0.10187(8) 0.40262(16) 1.0266(2) 0.0213(4) Uani 1 1 d .
H10A H 0.0884 0.4583 0.9406 0.032 Uiso 1 1 calc R
H10B H 0.1268 0.4478 1.1029 0.032 Uiso 1 1 calc R
H10C H 0.0679 0.3693 1.0847 0.032 Uiso 1 1 calc R
C11 C 0.29629(8) 0.17194(19) 0.9615(3) 0.0298(5) Uani 1 1 d .
H11A H 0.3121 0.0982 0.9092 0.045 Uiso 1 1 calc R
H11B H 0.3018 0.1660 1.0795 0.045 Uiso 1 1 calc R
H11C H 0.3168 0.2447 0.9204 0.045 Uiso 1 1 calc R
C12 C 0.11162(7) 0.00685(17) 0.6786(2) 0.0199(4) Uani 1 1 d .
H12A H 0.1401 -0.0574 0.6514 0.030 Uiso 1 1 calc R
H12B H 0.0972 0.0450 0.5783 0.030 Uiso 1 1 calc R
H12C H 0.0787 -0.0295 0.7381 0.030 Uiso 1 1 calc R
F1 F 0.0000 0.08792(13) 0.4328(2) 0.0252(4) Uani 1 2 d S
F2 F 0.0000 0.24853(16) 0.25081(19) 0.0310(4) Uani 1 2 d S
N1 N 0.04924(6) 0.22918(12) 0.79663(18) 0.0145(3) Uani 1 1 d .
O1 O 0.05206(5) 0.27346(11) 0.50420(16) 0.0188(3) Uani 1 1 d .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
F2 B1 F1 108.3(2) . .
F2 B1 O1 111.33(15) . 4
F1 B1 O1 110.91(15) . 4
F2 B1 O1 111.33(15) . .
F1 B1 O1 110.91(15) . .
O1 B1 O1 104.1(2) 4 .
N1 C1 N1 114.2(2) . 4
N1 C1 H1 122.9 . .
N1 C1 H1 122.9 4 .
O1 C2 N1 113.90(13) . .
O1 C2 C2 106.51(8) . 4
N1 C2 C2 102.59(8) . 4
O1 C2 H2 111.1 . .
N1 C2 H2 111.1 . .
C2 C2 H2 111.1 4 .
C5 C4 C9 122.52(14) . .
C5 C4 N1 117.97(14) . .
C9 C4 N1 119.37(14) . .
C6 C5 C4 117.72(14) . .
C6 C5 C10 120.49(16) . .
C4 C5 C10 121.75(15) . .
C5 C6 C7 122.25(16) . .
C5 C6 H6 118.9 . .
C7 C6 H6 118.9 . .
C6 C7 C8 117.95(15) . .
C6 C7 C11 120.59(16) . .
C8 C7 C11 121.46(16) . .
C7 C8 C9 122.41(15) . .
C7 C8 H8 118.8 . .
C9 C8 H8 118.8 . .
C4 C9 C8 117.08(15) . .
C4 C9 C12 122.40(14) . .
C8 C9 C12 120.51(15) . .
C5 C10 H10A 109.5 . .
C5 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C5 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C1 N1 C4 128.28(16) . .
C1 N1 C2 110.30(14) . .
C4 N1 C2 121.27(12) . .
C2 O1 B1 109.31(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F2 1.385(3) .
B1 F1 1.395(3) .
B1 O1 1.477(2) 4
B1 O1 1.477(2) .
C1 N1 1.3119(19) .
C1 N1 1.3119(19) 4
C1 H1 0.9300 .
C2 O1 1.369(2) .
C2 N1 1.496(2) .
C2 C2 1.551(3) 4
C2 H2 0.9800 .
C4 C5 1.391(2) .
C4 C9 1.394(2) .
C4 N1 1.444(2) .
C5 C6 1.385(2) .
C5 C10 1.510(2) .
C6 C7 1.387(2) .
C6 H6 0.9300 .
C7 C8 1.387(3) .
C7 C11 1.506(2) .
C8 C9 1.394(2) .
C8 H8 0.9300 .
C9 C12 1.501(2) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_1
C9 C4 C5 C6 2.2(2) .
N1 C4 C5 C6 -173.56(15) .
C9 C4 C5 C10 -175.77(16) .
N1 C4 C5 C10 8.5(2) .
C4 C5 C6 C7 -0.8(3) .
C10 C5 C6 C7 177.19(17) .
C5 C6 C7 C8 -1.6(3) .
C5 C6 C7 C11 178.89(18) .
C6 C7 C8 C9 2.7(3) .
C11 C7 C8 C9 -177.79(16) .
C5 C4 C9 C8 -1.1(2) .
N1 C4 C9 C8 174.53(15) .
C5 C4 C9 C12 178.06(16) .
N1 C4 C9 C12 -6.3(2) .
C7 C8 C9 C4 -1.4(2) .
C7 C8 C9 C12 179.43(17) .
N1 C1 N1 C4 175.77(11) 4
N1 C1 N1 C2 0.3(3) 4
C5 C4 N1 C1 -94.7(2) .
C9 C4 N1 C1 89.5(2) .
C5 C4 N1 C2 80.39(19) .
C9 C4 N1 C2 -95.47(18) .
O1 C2 N1 C1 -114.84(17) .
C2 C2 N1 C1 -0.16(15) 4
O1 C2 N1 C4 69.30(19) .
C2 C2 N1 C4 -176.01(12) 4
N1 C2 O1 B1 99.55(17) .
C2 C2 O1 B1 -12.79(15) 4
F2 B1 O1 C2 140.22(17) .
F1 B1 O1 C2 -99.13(19) .
O1 B1 O1 C2 20.2(2) 4
