#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507550.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_1507550
loop_
_publ_author_name
'Ellis, Keisha K.'
'Wilke, Burkhardt'
'Zhang, Yuegang'
'Diver, Steven T.'
_publ_section_title
;
 A New Method for the Synthesis of Imidazolidinone- and
 Benzimidazolone-Containing [2.2]Cyclophanes
;
_journal_issue                   24
_journal_name_full               'Organic Letters'
_journal_page_first              3785
_journal_paper_doi               10.1021/ol0064866
_journal_volume                  2
_journal_year                    2000
_chemical_formula_sum            'C19 H20 N2 O S2'
_chemical_formula_weight         356.49
_chemical_melting_point          224.2(8)
_chemical_name_common            Diver-5B
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 129.37(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.300(6)
_cell_length_b                   9.3010(19)
_cell_length_c                   17.584(4)
_cell_measurement_reflns_used    3300
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      3.20
_cell_volume                     3452(2)
_computing_cell_refinement       DENZO
_computing_data_collection       XPRESS
_computing_data_reduction        SCALEPACK
_computing_molecular_graphics    SHELXL-XP
_computing_publication_material  SHELXL-XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'DIP-2000 diffractometer'
_diffrn_measurement_method       'oscillation photo around ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6405
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0092(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0531P)²+2.6933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3398
_reflns_number_total             3606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0064866.cif
_cod_data_source_block           Diver-5B
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '223.5-225' was changed to '224.2(8)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3451.5(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1507550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S1 S 0.06304(2) 0.61780(5) 1.06871(3) 0.04830(16) Uani 1 1 d
S2 S 0.17211(2) 1.08376(5) 0.89685(3) 0.04780(16) Uani 1 1 d
N1 N 0.07258(6) 0.93193(12) 0.86231(9) 0.0309(3) Uani 1 1 d
O1 O 0.01991(5) 1.02976(12) 0.91480(9) 0.0412(3) Uani 1 1 d
N2 N 0.03767(6) 0.78366(12) 0.91705(9) 0.0310(3) Uani 1 1 d
C1 C 0.04141(6) 0.92751(15) 0.90085(10) 0.0301(3) Uani 1 1 d
C8 C 0.08964(8) 1.06640(17) 0.84267(13) 0.0398(4) Uani 1 1 d
C2 C 0.08509(6) 0.79249(15) 0.84934(10) 0.0313(3) Uani 1 1 d
C7 C 0.06259(6) 0.69911(15) 0.88343(10) 0.0311(3) Uani 1 1 d
C16 C 0.14104(8) 0.98295(18) 1.13558(12) 0.0412(4) Uani 1 1 d
C9 C 0.01220(8) 0.73616(18) 0.96431(13) 0.0406(4) Uani 1 1 d
C15 C 0.15354(8) 0.83696(17) 1.14246(11) 0.0396(4) Uani 1 1 d
C13 C 0.21235(7) 0.88535(18) 1.08723(13) 0.0409(4) Uani 1 1 d
C3 C 0.11247(8) 0.7422(2) 0.81031(13) 0.0436(4) Uani 1 1 d
C17 C 0.16240(8) 1.08262(16) 1.10335(12) 0.0393(4) Uani 1 1 d
C12 C 0.19632(7) 1.03091(17) 1.07467(11) 0.0381(4) Uani 1 1 d
C14 C 0.19251(7) 0.78668(17) 1.12169(11) 0.0397(4) Uani 1 1 d
C10 C 0.21360(10) 1.1270(2) 1.02592(14) 0.0535(5) Uani 1 1 d
C6 C 0.06635(9) 0.55114(17) 0.87806(13) 0.0438(4) Uani 1 1 d
C5 C 0.09400(10) 0.5006(2) 0.83869(15) 0.0545(5) Uani 1 1 d
C11 C 0.12189(12) 0.7390(2) 1.16781(15) 0.0583(6) Uani 1 1 d
C4 C 0.11657(9) 0.5935(2) 0.80561(16) 0.0533(5) Uani 1 1 d
C18 C 0.14688(14) 1.2397(2) 1.0996(2) 0.0648(6) Uani 1 1 d
C19 C 0.21113(12) 0.6310(2) 1.13265(19) 0.0635(6) Uani 1 1 d
H1 H 0.0038(10) 0.823(2) 0.9889(16) 0.058(6) Uiso 1 1 d
H2 H 0.2371(9) 0.851(2) 1.0683(16) 0.051(5) Uiso 1 1 d
H3 H -0.0269(9) 0.679(2) 0.9181(14) 0.041(5) Uiso 1 1 d
H4 H 0.1136(10) 1.018(2) 1.1517(15) 0.053(6) Uiso 1 1 d
H5 H 0.0763(9) 1.145(2) 0.8654(15) 0.049(5) Uiso 1 1 d
H6 H 0.0683(10) 1.074(2) 0.7725(17) 0.049(5) Uiso 1 1 d
H7 H 0.2583(12) 1.111(2) 1.051(2) 0.073(7) Uiso 1 1 d
H8 H 0.0501(10) 0.492(3) 0.9004(16) 0.058(6) Uiso 1 1 d
H9 H 0.1264(10) 0.805(2) 0.7831(17) 0.061(6) Uiso 1 1 d
H10 H 0.1531(11) 0.676(3) 1.2210(19) 0.065(7) Uiso 1 1 d
H11 H 0.1369(10) 0.555(2) 0.7787(18) 0.063(6) Uiso 1 1 d
H12 H 0.0981(11) 0.402(3) 0.8326(19) 0.073(7) Uiso 1 1 d
H13 H 0.1133(14) 1.265(3) 1.039(2) 0.086(9) Uiso 1 1 d
H14 H 0.2240(17) 0.590(4) 1.193(3) 0.120(12) Uiso 1 1 d
H15 H 0.1774(15) 0.572(3) 1.082(2) 0.095(9) Uiso 1 1 d
H16 H 0.1828(17) 1.291(4) 1.128(3) 0.120(12) Uiso 1 1 d
H17 H 0.1068(14) 0.784(4) 1.193(3) 0.104(11) Uiso 1 1 d
H18 H 0.2434(17) 0.621(3) 1.134(3) 0.100(11) Uiso 1 1 d
H19 H 0.2062(12) 1.230(3) 1.031(2) 0.085(8) Uiso 1 1 d
H20 H 0.1335(15) 1.260(4) 1.139(2) 0.113(12) Uiso 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'
S S 0.1246 0.1234 '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
C9 S1 C11 103.68(10)
C8 S2 C10 104.92(10)
C1 N1 C2 110.02(11)
C1 N1 C8 122.14(13)
C2 N1 C8 127.83(14)
C1 N2 C7 109.78(12)
C1 N2 C9 122.47(13)
C7 N2 C9 127.74(13)
O1 C1 N1 126.74(13)
O1 C1 N2 127.10(14)
N1 C1 N2 106.12(12)
N1 C8 S2 115.55(11)
C3 C2 N1 131.50(15)
C3 C2 C7 121.79(14)
N1 C2 C7 106.70(13)
C6 C7 N2 131.73(14)
C6 C7 C2 121.00(15)
N2 C7 C2 107.25(12)
C15 C16 C17 122.95(16)
N2 C9 S1 115.38(12)
C16 C15 C14 119.21(14)
C16 C15 C11 117.56(18)
C14 C15 C11 123.17(17)
C14 C13 C12 122.76(16)
C2 C3 C4 117.08(17)
C12 C17 C16 117.66(15)
C12 C17 C18 123.43(17)
C16 C17 C18 118.91(18)
C17 C12 C13 119.44(15)
C17 C12 C10 121.46(17)
C13 C12 C10 119.03(17)
C13 C14 C15 117.61(15)
C13 C14 C19 119.93(19)
C15 C14 C19 122.43(18)
C12 C10 S2 113.91(12)
C7 C6 C5 117.12(17)
C4 C5 C6 121.67(17)
C15 C11 S1 114.45(13)
C5 C4 C3 121.34(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.8099(19)
S1 C11 1.827(2)
S2 C8 1.8114(18)
S2 C10 1.826(2)
N1 C1 1.3844(19)
N1 C2 1.3961(18)
N1 C8 1.4508(18)
O1 C1 1.2214(18)
N2 C1 1.3852(17)
N2 C7 1.3932(19)
N2 C9 1.4500(19)
C2 C3 1.378(2)
C2 C7 1.399(2)
C7 C6 1.388(2)
C16 C15 1.387(2)
C16 C17 1.393(2)
C15 C14 1.406(3)
C15 C11 1.505(2)
C13 C14 1.385(2)
C13 C12 1.397(2)
C3 C4 1.394(3)
C17 C12 1.391(2)
C17 C18 1.511(3)
C12 C10 1.507(2)
C14 C19 1.506(3)
C6 C5 1.390(3)
C5 C4 1.385(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 9489259 ChemSpider
