#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503830.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_1503830
loop_
_publ_author_name
'Lee, Hayan'
'Lee, Shim Sung'
_publ_section_title
;
 Thiaoxaaza-macrocyclic chromoionophores as mercury(II) sensors: synthesis
 and color modulation.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1393
_journal_page_last               1396
_journal_paper_doi               10.1021/ol900241p
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C37 H35 N5 O4 S2'
_chemical_formula_weight         677.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.657(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   36.187(4)
_cell_length_b                   16.3790(19)
_cell_length_c                   8.3869(10)
_cell_measurement_reflns_used    5637
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.46
_cell_volume                     4914.3(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.1076
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20962
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.9326
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    0.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.1052
_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)+(0.1231P)²+7.9515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2482
_refine_ls_wR_factor_ref         0.2713
_reflns_number_gt                3713
_reflns_number_total             5543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900241p_si_002.cif
_cod_data_source_block           aaa
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               1503830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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
N1 N 0.72781(12) 0.5000 0.6343(5) 0.0322(10) Uani 1 2 d S
N2 N 0.77053(12) 0.5000 0.1790(5) 0.0331(10) Uani 1 2 d S
N3 N 0.9088(2) 0.4727(6) -0.0469(10) 0.051(3) Uani 0.50 1 d P
N4 N 0.9233(2) 0.5380(6) -0.0878(10) 0.048(2) Uani 0.50 1 d P
N5 N 1.05563(17) 0.5000 -0.3609(8) 0.092(3) Uani 1 2 d S
S1 S 0.70622(3) 0.70604(6) 0.08096(11) 0.0377(3) Uani 1 1 d .
O1 O 0.70348(7) 0.65467(15) 0.4757(3) 0.0374(6) Uani 1 1 d .
O2 O 1.06913(13) 0.5648(4) -0.3885(7) 0.136(2) Uani 1 1 d .
C1 C 0.80487(16) 0.5000 0.6449(6) 0.0400(13) Uani 1 2 d S
H1A H 0.8313 0.5000 0.6515 0.048 Uiso 1 2 calc SR
C2 C 0.78534(11) 0.5722(2) 0.6400(4) 0.0377(9) Uani 1 1 d .
H2A H 0.7980 0.6230 0.6389 0.045 Uiso 1 1 calc R
C3 C 0.74725(10) 0.5702(2) 0.6367(4) 0.0302(8) Uani 1 1 d .
C4 C 0.72405(12) 0.6464(2) 0.6347(4) 0.0401(9) Uani 1 1 d .
H4A H 0.7067 0.6423 0.7150 0.048 Uiso 1 1 calc R
H4B H 0.7404 0.6945 0.6616 0.048 Uiso 1 1 calc R
C5 C 0.67633(10) 0.7151(2) 0.4539(4) 0.0344(8) Uani 1 1 d .
C6 C 0.66814(11) 0.7668(2) 0.5740(4) 0.0397(9) Uani 1 1 d .
H6A H 0.6819 0.7633 0.6795 0.048 Uiso 1 1 calc R
C7 C 0.63984(11) 0.8236(3) 0.5399(5) 0.0479(11) Uani 1 1 d .
H7A H 0.6337 0.8582 0.6230 0.057 Uiso 1 1 calc R
C8 C 0.62060(12) 0.8303(3) 0.3873(5) 0.0544(12) Uani 1 1 d .
H8A H 0.6017 0.8705 0.3631 0.065 Uiso 1 1 calc R
C9 C 0.62895(11) 0.7781(3) 0.2685(5) 0.0454(10) Uani 1 1 d .
H9A H 0.6150 0.7822 0.1634 0.054 Uiso 1 1 calc R
C10 C 0.65663(10) 0.7206(2) 0.2969(4) 0.0356(9) Uani 1 1 d .
C11 C 0.66621(10) 0.6671(2) 0.1656(4) 0.0371(9) Uani 1 1 d .
H11A H 0.6444 0.6633 0.0791 0.044 Uiso 1 1 calc R
H11B H 0.6719 0.6115 0.2086 0.044 Uiso 1 1 calc R
C12 C 0.73117(11) 0.6128(2) 0.0477(4) 0.0378(9) Uani 1 1 d .
H12A H 0.7132 0.5722 -0.0063 0.045 Uiso 1 1 calc R
H12B H 0.7497 0.6246 -0.0251 0.045 Uiso 1 1 calc R
C13 C 0.75136(10) 0.5764(2) 0.2048(4) 0.0330(8) Uani 1 1 d .
H13A H 0.7698 0.6163 0.2571 0.040 Uiso 1 1 calc R
H13B H 0.7330 0.5662 0.2789 0.040 Uiso 1 1 calc R
C14 C 0.80392(15) 0.5000 0.1209(6) 0.0351(12) Uani 1 2 d S
C15 C 0.82213(11) 0.4263(3) 0.0913(4) 0.0412(9) Uani 1 1 d .
H15A H 0.8105 0.3757 0.1087 0.049 Uiso 1 1 calc R
C16 C 0.85603(12) 0.4264(3) 0.0384(5) 0.0521(11) Uani 1 1 d .
H16A H 0.8679 0.3762 0.0212 0.063 Uiso 1 1 calc R
C17 C 0.87332(17) 0.5000 0.0095(7) 0.0589(19) Uani 1 2 d S
C18 C 0.9571(2) 0.5000 -0.1556(9) 0.124(6) Uani 1 2 d S
C19 C 0.97272(16) 0.4289(7) -0.1881(8) 0.121(3) Uani 1 1 d .
H19A H 0.9615 0.3789 -0.1639 0.145 Uiso 1 1 calc R
C20A C 1.00531(15) 0.4285(5) -0.2573(7) 0.091(2) Uani 1 1 d .
H20A H 1.0164 0.3784 -0.2820 0.109 Uiso 1 1 calc R
C21 C 1.02077(19) 0.5000 -0.2886(8) 0.073(2) Uani 1 2 d S
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 N1 C3 117.3(4) . 6_565
C14 N2 C13 121.1(2) . 6_565
C14 N2 C13 121.1(2) . .
C13 N2 C13 117.6(4) 6_565 .
N4 N3 N3 104.7(14) 6_565 6_565
N4 N3 N4 72.6(15) 6_565 .
N3 N3 N4 32.1(4) 6_565 .
N4 N3 C17 168.8(16) 6_565 .
N3 N3 C17 72.7(4) 6_565 .
N4 N3 C17 104.2(6) . .
N3 N4 N4 75.3(14) 6_565 6_565
N3 N4 N3 43.3(14) 6_565 .
N4 N4 N3 32.1(4) 6_565 .
N3 N4 C18 141.1(17) 6_565 .
N4 N4 C18 66.4(4) 6_565 .
N3 N4 C18 98.2(6) . .
O2 N5 O2 123.4(8) . 6_565
O2 N5 C21 118.3(4) . .
O2 N5 C21 118.3(4) 6_565 .
C12 S1 C11 102.02(18) . .
C5 O1 C4 116.6(3) . .
C2 C1 C2 118.6(5) 6_565 .
C3 C2 C1 119.2(4) . .
N1 C3 C2 122.8(3) . .
N1 C3 C4 114.8(3) . .
C2 C3 C4 122.4(3) . .
O1 C4 C3 107.4(3) . .
C6 C5 O1 124.6(3) . .
C6 C5 C10 120.6(3) . .
O1 C5 C10 114.8(3) . .
C7 C6 C5 119.7(4) . .
C8 C7 C6 120.4(4) . .
C7 C8 C9 119.4(4) . .
C10 C9 C8 122.3(4) . .
C9 C10 C5 117.6(3) . .
C9 C10 C11 121.5(3) . .
C5 C10 C11 121.0(3) . .
C10 C11 S1 111.7(3) . .
C13 C12 S1 112.3(2) . .
N2 C13 C12 112.4(3) . .
N2 C14 C15 121.4(2) . 6_565
N2 C14 C15 121.4(2) . .
C15 C14 C15 117.1(5) 6_565 .
C16 C15 C14 121.3(4) . .
C15 C16 C17 120.4(4) . .
C16 C17 C16 119.4(5) 6_565 .
C16 C17 N3 137.6(5) 6_565 .
C16 C17 N3 103.0(4) . .
C16 C17 N3 103.0(4) 6_565 6_565
C16 C17 N3 137.6(5) . 6_565
N3 C17 N3 34.6(7) . 6_565
C19 C18 C19 120.6(9) 6_565 .
C19 C18 N4 143.3(7) 6_565 6_565
C19 C18 N4 96.1(5) . 6_565
C19 C18 N4 96.1(5) 6_565 .
C19 C18 N4 143.3(7) . .
N4 C18 N4 47.2(8) 6_565 .
C18 C19 C20A 120.0(9) . .
C21 C20A C19 118.8(8) . .
C20A C21 C20A 121.7(8) 6_565 .
C20A C21 N5 119.1(4) 6_565 .
C20A C21 N5 119.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.346(4) .
N1 C3 1.346(4) 6_565
N2 C14 1.369(7) .
N2 C13 1.462(4) 6_565
N2 C13 1.462(4) .
N3 N4 0.692(8) 6_565
N3 N3 0.894(19) 6_565
N3 N4 1.261(9) .
N3 C17 1.501(10) .
N4 N3 0.692(8) 6_565
N4 N4 1.24(2) 6_565
N4 C18 1.553(11) .
N5 O2 1.205(6) .
N5 O2 1.205(6) 6_565
N5 C21 1.480(9) .
S1 C12 1.818(4) .
S1 C11 1.821(4) .
O1 C5 1.387(4) .
O1 C4 1.432(4) .
C1 C2 1.376(5) 6_565
C1 C2 1.376(5) .
C2 C3 1.375(5) .
C3 C4 1.503(5) .
C5 C6 1.382(5) .
C5 C10 1.403(5) .
C6 C7 1.381(5) .
C7 C8 1.366(6) .
C8 C9 1.380(6) .
C9 C10 1.369(5) .
C10 C11 1.488(5) .
C12 C13 1.528(5) .
C14 C15 1.415(5) 6_565
C14 C15 1.415(5) .
C15 C16 1.366(6) .
C16 C17 1.395(6) .
C17 C16 1.395(6) 6_565
C17 N3 1.501(10) 6_565
C18 C19 1.340(10) 6_565
C18 C19 1.340(10) .
C18 N4 1.553(11) 6_565
C19 C20A 1.391(8) .
C20A C21 1.341(7) .
C21 C20A 1.341(7) 6_565
