#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/19/7001981.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_7001981
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         'C19 H24 N3, I'
_chemical_formula_sum            'C19 H24 I N3'
_chemical_formula_weight         421.31
_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                 104.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.432(3)
_cell_length_b                   17.575(4)
_cell_length_c                   7.9907(16)
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.95
_cell_volume                     1828.6(7)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6579
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0269
_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)+(0.0065P)²+1.6367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0591
_reflns_number_gt                3436
_reflns_number_total             3964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b909834h.txt
_cod_data_source_block           asKJC40
_cod_original_cell_volume        1828.6(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7001981
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
I1 I 0.311617(12) 0.075408(8) 0.78471(2) 0.02311(6) Uani 1 1 d . . .
N1 N 0.84815(15) 0.39292(10) 0.4537(2) 0.0172(4) Uani 1 1 d . . .
C1 C 0.78130(18) 0.33710(13) 0.4272(3) 0.0178(5) Uani 1 1 d . . .
H1 H 0.8071 0.2878 0.4621 0.021 Uiso 1 1 calc R . .
N2 N 0.68140(15) 0.34249(10) 0.3567(2) 0.0176(4) Uani 1 1 d . . .
C2 C 0.83036(19) 0.46995(13) 0.3707(3) 0.0210(5) Uani 1 1 d . . .
H2A H 0.8969 0.4913 0.3610 0.025 Uiso 1 1 calc R . .
H2B H 0.8017 0.5043 0.4452 0.025 Uiso 1 1 calc R . .
N3 N 0.67772(16) 0.20959(11) 0.3419(3) 0.0224(5) Uani 1 1 d . . .
C3 C 0.7571(2) 0.46675(14) 0.1923(3) 0.0232(5) Uani 1 1 d . . .
H3A H 0.7727 0.4208 0.1316 0.028 Uiso 1 1 calc R . .
H3B H 0.7692 0.5117 0.1253 0.028 Uiso 1 1 calc R . .
C4 C 0.6440(2) 0.46489(14) 0.1963(3) 0.0236(5) Uani 1 1 d . . .
H4A H 0.6198 0.5174 0.2077 0.028 Uiso 1 1 calc R . .
H4B H 0.6028 0.4435 0.0864 0.028 Uiso 1 1 calc R . .
C5 C 0.62847(19) 0.41701(12) 0.3458(3) 0.0207(5) Uani 1 1 d . . .
H5A H 0.6548 0.4452 0.4550 0.025 Uiso 1 1 calc R . .
H5B H 0.5541 0.4084 0.3320 0.025 Uiso 1 1 calc R . .
C6 C 0.95289(18) 0.37411(12) 0.5471(3) 0.0170(5) Uani 1 1 d . . .
C7 C 0.98115(18) 0.38540(12) 0.7262(3) 0.0182(5) Uani 1 1 d . . .
C8 C 1.08193(19) 0.36588(13) 0.8116(3) 0.0193(5) Uani 1 1 d . . .
H8 H 1.1036 0.3728 0.9330 0.023 Uiso 1 1 calc R . .
C9 C 1.15115(19) 0.33680(13) 0.7250(3) 0.0201(5) Uani 1 1 d . . .
C10 C 1.1194(2) 0.32734(13) 0.5471(3) 0.0229(5) Uani 1 1 d . . .
H10 H 1.1666 0.3078 0.4867 0.027 Uiso 1 1 calc R . .
C11 C 1.0201(2) 0.34575(13) 0.4549(3) 0.0216(5) Uani 1 1 d . . .
C12 C 0.9070(2) 0.41572(16) 0.8233(3) 0.0292(6) Uani 1 1 d . . .
H12A H 0.8670 0.4573 0.7575 0.044 Uiso 1 1 calc R . .
H12B H 0.9452 0.4347 0.9361 0.044 Uiso 1 1 calc R . .
H12C H 0.8606 0.3749 0.8395 0.044 Uiso 1 1 calc R . .
C13 C 1.2599(2) 0.31650(14) 0.8184(4) 0.0272(6) Uani 1 1 d . . .
H13A H 1.2684 0.3227 0.9430 0.041 Uiso 1 1 calc R . .
H13B H 1.3079 0.3501 0.7796 0.041 Uiso 1 1 calc R . .
H13C H 1.2738 0.2635 0.7932 0.041 Uiso 1 1 calc R . .
C14 C 0.9893(2) 0.33467(17) 0.2617(3) 0.0363(7) Uani 1 1 d . . .
H14A H 0.9392 0.2932 0.2333 0.054 Uiso 1 1 calc R . .
H14B H 1.0501 0.3219 0.2203 0.054 Uiso 1 1 calc R . .
H14C H 0.9586 0.3817 0.2062 0.054 Uiso 1 1 calc R . .
C15 C 0.62532(18) 0.27351(13) 0.2961(3) 0.0176(5) Uani 1 1 d . . .
C16 C 0.52661(19) 0.27748(14) 0.1924(3) 0.0226(5) Uani 1 1 d . . .
H16 H 0.4926 0.3248 0.1631 0.027 Uiso 1 1 calc R . .
C17 C 0.4794(2) 0.20877(14) 0.1331(3) 0.0250(6) Uani 1 1 d . . .
H17 H 0.4119 0.2084 0.0603 0.030 Uiso 1 1 calc R . .
C18 C 0.53091(19) 0.14120(14) 0.1802(3) 0.0234(5) Uani 1 1 d . . .
H18 H 0.4993 0.0938 0.1421 0.028 Uiso 1 1 calc R . .
C19 C 0.6294(2) 0.14411(14) 0.2840(3) 0.0237(5) Uani 1 1 d . . .
H19 H 0.6650 0.0976 0.3163 0.028 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'
I I -0.4742 1.8119 '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
C1 N1 C6 116.68(18) . . ?
C1 N1 C2 125.11(19) . . ?
C6 N1 C2 117.34(18) . . ?
N1 C1 N2 126.6(2) . . ?
C1 N2 C15 118.17(19) . . ?
C1 N2 C5 120.61(19) . . ?
C15 N2 C5 121.19(19) . . ?
N1 C2 C3 112.14(18) . . ?
C15 N3 C19 116.8(2) . . ?
C2 C3 C4 113.5(2) . . ?
C5 C4 C3 111.0(2) . . ?
N2 C5 C4 112.3(2) . . ?
C11 C6 C7 122.9(2) . . ?
C11 C6 N1 118.7(2) . . ?
C7 C6 N1 118.4(2) . . ?
C8 C7 C6 116.7(2) . . ?
C8 C7 C12 121.3(2) . . ?
C6 C7 C12 122.0(2) . . ?
C9 C8 C7 122.3(2) . . ?
C8 C9 C10 118.7(2) . . ?
C8 C9 C13 121.7(2) . . ?
C10 C9 C13 119.6(2) . . ?
C9 C10 C11 121.7(2) . . ?
C6 C11 C10 117.7(2) . . ?
C6 C11 C14 122.5(2) . . ?
C10 C11 C14 119.8(2) . . ?
N3 C15 C16 125.0(2) . . ?
N3 C15 N2 114.80(19) . . ?
C16 C15 N2 120.2(2) . . ?
C15 C16 C17 116.8(2) . . ?
C18 C17 C16 119.9(2) . . ?
C19 C18 C17 118.4(2) . . ?
N3 C19 C18 123.3(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 C1 1.312(3) . ?
N1 C6 1.459(3) . ?
N1 C2 1.501(3) . ?
C1 N2 1.325(3) . ?
N2 C15 1.447(3) . ?
N2 C5 1.483(3) . ?
C2 C3 1.521(3) . ?
N3 C15 1.329(3) . ?
N3 C19 1.346(3) . ?
C3 C4 1.528(4) . ?
C4 C5 1.517(3) . ?
C6 C11 1.390(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.401(3) . ?
C7 C12 1.502(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.390(3) . ?
C9 C13 1.511(3) . ?
C10 C11 1.394(3) . ?
C11 C14 1.509(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.379(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25946146
