#------------------------------------------------------------------------------
#$Date: 2017-12-05 15:19:23 +0200 (Tue, 05 Dec 2017) $
#$Revision: 203991 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/77/1547779.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_1547779
loop_
_publ_author_name
'Shimizu, Akinori'
'Inoue, Yoshihisa'
'Mori, Tadashi'
_publ_section_title
;
 A Combined Experimental and Theoretical Study on the Circular Dichroism
 of Staggered and Eclipsed Forms of Dimethoxy[2.2]-, [3.2]-, and
 [3.3]Pyridinophanes and Their Protonated Forms.
;
_journal_issue                   44
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              8389
_journal_page_last               8398
_journal_paper_doi               10.1021/acs.jpca.7b08623
_journal_volume                  121
_journal_year                    2017
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C19 H23 Br N2 O2 S2'
_chemical_formula_sum            'C19 H23 Br N2 O2 S2'
_chemical_formula_weight         455.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.7380(3)
_cell_length_b                   17.0684(8)
_cell_length_c                   17.5974(7)
_cell_measurement_reflns_used    11280
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.02
_cell_volume                     2023.82(15)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19372
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         4.024
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.259
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(Walker & Stuart, 1983)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             936.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.150
_refine_diff_density_min         -1.480
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1963 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.000(11)
_refine_ls_extinction_coef       77(23)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2899
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0010Fo² + 1.0000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0466
_reflns_number_gt                2899
_reflns_number_total             4590
_reflns_threshold_expression     F>2.0σ(F)
_cod_data_source_file            jp7b08623_si_004.cif
_cod_data_source_block           PyP-OMe-st-H+/MeCN
_cod_depositor_comments
'Adding full bibliography for 1547777--1547780.cif.'
_cod_original_cell_volume        2023.83(16)
_cod_database_code               1547779
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -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_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br(1) Br 1.15184(8) -0.10082(3) -0.05696(3) 0.03003(15) Uani 1 4 d .
S(2) S 0.8412(2) 0.02335(7) 0.34533(6) 0.0243(3) Uani 1 4 d .
S(3) S 0.6759(2) 0.18481(7) -0.01993(7) 0.0260(4) Uani 1 4 d .
O(4) O 0.6451(5) -0.10746(18) 0.16702(16) 0.0267(9) Uani 1 4 d .
O(5) O 0.4087(5) 0.20112(18) 0.13997(17) 0.0239(9) Uani 1 4 d .
N(1) N 1.6301(8) -0.2939(3) -0.2104(3) 0.0463(16) Uani 1 4 d .
N(6) N 1.0211(6) 0.0236(2) 0.0708(2) 0.0225(12) Uani 1 4 d .
C(1) C 1.6406(9) -0.2634(3) -0.1534(3) 0.0344(16) Uani 1 4 d .
C(2) C 1.6528(10) -0.2250(3) -0.0799(3) 0.0364(16) Uani 1 4 d .
C(7) C 0.5058(7) 0.0904(3) 0.2202(3) 0.0191(13) Uani 1 4 d .
C(8) C 0.5460(7) 0.0038(3) 0.0883(3) 0.0187(13) Uani 1 4 d .
C(9) C 0.9565(7) 0.0971(3) 0.0621(2) 0.0210(13) Uani 1 4 d .
C(10) C 0.5835(7) -0.0318(3) 0.1581(3) 0.0176(13) Uani 1 4 d .
C(11) C 0.4663(7) 0.1252(3) 0.1498(3) 0.0197(13) Uani 1 4 d .
C(12) C 0.8940(7) 0.1229(3) -0.0172(3) 0.0267(15) Uani 1 4 d .
C(13) C 0.9786(7) 0.1113(3) 0.1961(3) 0.0214(13) Uani 1 4 d .
C(14) C 0.9442(8) 0.1436(3) 0.1264(3) 0.0246(14) Uani 1 4 d .
C(15) C 0.4925(7) 0.0816(3) 0.0837(2) 0.0160(13) Uani 1 4 d .
C(16) C 0.5672(7) 0.0131(3) 0.2247(3) 0.0187(13) Uani 1 4 d .
C(18) C 1.0275(7) 0.0330(3) 0.2049(3) 0.0237(14) Uani 1 4 d .
C(19) C 1.0399(7) -0.0059(3) 0.2829(3) 0.0277(15) Uani 1 4 d .
C(20) C 0.6469(9) -0.1554(3) 0.1002(3) 0.0295(14) Uani 1 4 d .
C(21) C 0.6233(8) -0.0219(3) 0.3015(3) 0.0264(14) Uani 1 4 d .
C(24) C 0.4732(7) 0.1199(3) 0.0059(3) 0.0242(14) Uani 1 4 d .
C(25) C 0.3734(8) 0.2470(3) 0.2071(3) 0.0299(15) Uani 1 4 d .
C(26) C 1.0571(7) -0.0101(3) 0.1397(3) 0.0228(14) Uani 1 4 d .
H(1) H 1.03739 -0.0106 0.02971 0.0271 Uiso 1 4 calc R
H(2) H 0.5572 -0.02541 0.04388 0.0223 Uiso 1 4 calc R
H(3) H 0.55246 -0.13686 0.06295 0.0354 Uiso 1 4 calc R
H(4) H 0.885 0.07186 -0.04255 0.0320 Uiso 1 4 calc R
H(5) H 0.63496 -0.07664 0.28748 0.0317 Uiso 1 4 calc R
H(6) H 0.49794 -0.0168 0.32815 0.0318 Uiso 1 4 calc R
H(7) H 0.34292 0.1434 0.0114 0.0292 Uiso 1 4 calc R
H(8) H 0.49075 0.11974 0.26433 0.0229 Uiso 1 4 calc R
H(9) H 1.01819 0.14686 -0.0344 0.0321 Uiso 1 4 calc R
H(10) H 0.96952 0.14221 0.23952 0.0256 Uiso 1 4 calc R
H(11) H 1.17566 0.00935 0.29642 0.0333 Uiso 1 4 calc R
H(12) H 0.91212 0.19642 0.12208 0.0295 Uiso 1 4 calc R
H(13) H 1.04902 -0.06092 0.26757 0.0333 Uiso 1 4 calc R
H(14) H 0.61353 -0.20962 0.11326 0.0355 Uiso 1 4 calc R
H(15) H 0.77979 -0.15369 0.07761 0.0355 Uiso 1 4 calc R
H(16) H 0.45465 0.07336 -0.02498 0.0291 Uiso 1 4 calc R
H(17) H 0.49214 0.24949 0.23717 0.0361 Uiso 1 4 calc R
H(18) H 0.33407 0.299 0.19284 0.0360 Uiso 1 4 calc R
H(19) H 0.26944 0.22298 0.23625 0.0359 Uiso 1 4 calc R
H(20) H 1.10215 -0.06156 0.14182 0.0274 Uiso 1 4 calc R
H(21) H 1.77545 -0.19662 -0.07645 0.0437 Uiso 1 4 calc R
H(22) H 1.54362 -0.18936 -0.07436 0.0438 Uiso 1 4 calc R
H(23) H 1.6475 -0.26364 -0.04029 0.0437 Uiso 1 4 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 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_publ_flag
C(19) S(2) C(21) 102.9(2) yes
C(12) S(3) C(24) 104.3(2) yes
C(10) O(4) C(20) 116.7(3) yes
C(11) O(5) C(25) 117.4(3) yes
C(9) N(6) C(26) 123.8(4) yes
N(1) C(1) C(2) 179.4(6) yes
C(11) C(7) C(16) 120.8(4) yes
C(10) C(8) C(15) 121.3(4) yes
N(6) C(9) C(12) 117.8(4) yes
N(6) C(9) C(14) 117.7(4) yes
C(12) C(9) C(14) 124.5(4) yes
O(4) C(10) C(8) 124.6(4) yes
O(4) C(10) C(16) 116.3(4) yes
C(8) C(10) C(16) 119.0(4) yes
O(5) C(11) C(7) 124.7(4) yes
O(5) C(11) C(15) 116.0(4) yes
C(7) C(11) C(15) 119.3(4) yes
S(3) C(12) C(9) 114.7(3) yes
C(14) C(13) C(18) 122.0(4) yes
C(9) C(14) C(13) 119.5(5) yes
C(8) C(15) C(11) 119.9(4) yes
C(8) C(15) C(24) 119.3(4) yes
C(11) C(15) C(24) 120.7(4) yes
C(7) C(16) C(10) 119.7(4) yes
C(7) C(16) C(21) 119.8(4) yes
C(10) C(16) C(21) 120.5(4) yes
C(13) C(18) C(19) 122.1(4) yes
C(13) C(18) C(26) 117.2(4) yes
C(19) C(18) C(26) 120.6(5) yes
S(2) C(19) C(18) 112.8(3) yes
S(2) C(21) C(16) 114.1(3) yes
S(3) C(24) C(15) 115.0(3) yes
N(6) C(26) C(18) 119.3(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(2) C(19) 1.801(5) yes
S(2) C(21) 1.829(5) yes
S(3) C(12) 1.811(5) yes
S(3) C(24) 1.817(5) yes
O(4) C(10) 1.365(6) yes
O(4) C(20) 1.432(5) yes
O(5) C(11) 1.364(5) yes
O(5) C(25) 1.437(6) yes
N(1) C(1) 1.133(8) yes
N(6) C(9) 1.336(6) yes
N(6) C(26) 1.363(6) yes
C(1) C(2) 1.452(7) yes
C(7) C(11) 1.399(6) yes
C(7) C(16) 1.385(7) yes
C(8) C(10) 1.393(6) yes
C(8) C(15) 1.378(6) yes
C(9) C(12) 1.523(6) yes
C(9) C(14) 1.385(6) yes
C(10) C(16) 1.404(6) yes
C(11) C(15) 1.393(6) yes
C(13) C(14) 1.364(6) yes
C(13) C(18) 1.386(7) yes
C(15) C(24) 1.522(6) yes
C(16) C(21) 1.525(6) yes
C(18) C(19) 1.528(7) yes
C(18) C(26) 1.378(7) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N(6) H(1) Br(1) 3.218(5) 0.936 2.302 165.7 no
