#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178481 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/02/4030235.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_4030235
loop_
_publ_author_name
'Gromov, Sergey P.'
'Vedernikov, Artem I.'
'Lobova, Natalia A.'
'Kuz'mina, Lyudmila G.'
'Dmitrieva, Svetlana N.'
'Strelenko, Yuri A.'
'Howard, Judith A. K.'
_publ_section_title
;
 Synthesis, structure, and properties of supramolecular photoswitches
 based on ammonioalkyl derivatives of crown ether styryl dyes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11416
_journal_page_last               11430
_journal_paper_doi               10.1021/jo5018074
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C31 H46 Br2 N2 O9'
_chemical_formula_weight         750.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.737(2)
_cell_angle_beta                 95.770(2)
_cell_angle_gamma                114.086(2)
_cell_formula_units_Z            2
_cell_length_a                   11.4310(11)
_cell_length_b                   11.6678(11)
_cell_length_c                   14.7274(14)
_cell_measurement_reflns_used    5445
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.948
_cell_measurement_theta_min      2.196
_cell_volume                     1687.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART-6K'
_diffrn_measurement_method       /W
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19380
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    2.456
_exptl_absorpt_correction_T_max  0.6662
_exptl_absorpt_correction_T_min  0.5071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.615
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.124
_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     468
_refine_ls_number_reflns         8811
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0593
_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)+(0.1100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1786
_reflns_number_gt                5974
_reflns_number_total             8811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5018074_si_002.cif
_cod_data_source_block           dye_1e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030234--4030240.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4030235
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.04607(4) 0.73618(4) 0.94268(3) 0.03396(14) Uani 1 1 d . . .
Br2 Br 0.46754(8) 0.7105(3) 0.31825(6) 0.0366(4) Uani 0.954(8) 1 d P A 1
Br3 Br 0.4855(16) 0.775(4) 0.3291(10) 0.033(5) Uani 0.046(8) 1 d P A 2
O1 O 1.0302(3) 0.9809(3) 0.71923(19) 0.0270(5) Uani 1 1 d . . .
O4 O 0.9772(3) 1.4147(4) 0.6698(3) 0.0520(9) Uani 1 1 d . . .
O5 O 0.7904(3) 1.1359(3) 0.5445(2) 0.0286(6) Uani 1 1 d . B .
O6 O 0.8773(3) 0.9507(2) 0.56678(18) 0.0261(5) Uani 1 1 d . . .
N2 N 0.0405(4) -0.3197(4) 0.1516(3) 0.0401(8) Uani 1 1 d . . .
H2A H -0.0441 -0.3554 0.1582 0.060 Uiso 1 1 calc R . .
H2B H 0.0813 -0.3663 0.1685 0.060 Uiso 1 1 calc R . .
H2C H 0.0407 -0.3234 0.0892 0.060 Uiso 1 1 calc R . .
N1 N 0.3210(3) 0.0185(3) 0.2575(2) 0.0255(6) Uani 1 1 d . . .
C1 C 0.3928(4) 0.0567(4) 0.3470(3) 0.0286(8) Uani 1 1 d . . .
H1 H 0.3910 -0.0093 0.3743 0.034 Uiso 1 1 calc R . .
C2 C 0.4680(4) 0.1865(4) 0.4001(3) 0.0285(8) Uani 1 1 d . . .
H2 H 0.5151 0.2088 0.4640 0.034 Uiso 1 1 calc R . .
C3 C 0.4776(3) 0.2874(4) 0.3631(3) 0.0255(7) Uani 1 1 d . . .
C4 C 0.3966(3) 0.2493(4) 0.2698(3) 0.0235(7) Uani 1 1 d . . .
C5 C 0.3902(4) 0.3422(4) 0.2264(3) 0.0275(8) Uani 1 1 d . . .
H5 H 0.4435 0.4344 0.2591 0.033 Uiso 1 1 calc R . .
C6 C 0.3089(4) 0.3018(4) 0.1387(3) 0.0317(8) Uani 1 1 d . . .
H6 H 0.3052 0.3661 0.1113 0.038 Uiso 1 1 calc R . .
C7 C 0.2307(4) 0.1666(4) 0.0882(3) 0.0334(9) Uani 1 1 d . . .
H7 H 0.1742 0.1399 0.0270 0.040 Uiso 1 1 calc R . .
C8 C 0.2348(4) 0.0732(4) 0.1260(3) 0.0280(8) Uani 1 1 d . . .
H8 H 0.1822 -0.0184 0.0910 0.034 Uiso 1 1 calc R . .
C9 C 0.3169(3) 0.1123(4) 0.2169(2) 0.0227(7) Uani 1 1 d . . .
C10 C 0.5663(4) 0.4247(4) 0.4162(3) 0.0300(8) Uani 1 1 d . . .
H10 H 0.5661 0.4902 0.3888 0.036 Uiso 1 1 calc R . .
C11 C 0.6490(4) 0.4652(4) 0.5020(3) 0.0277(8) Uani 1 1 d . . .
H11 H 0.6457 0.3979 0.5283 0.033 Uiso 1 1 calc R . .
C12 C 0.7430(3) 0.6009(4) 0.5591(3) 0.0231(7) Uani 1 1 d . . .
C13 C 0.8221(4) 0.6214(4) 0.6457(3) 0.0250(7) Uani 1 1 d . . .
H13 H 0.8090 0.5477 0.6671 0.030 Uiso 1 1 calc R . .
C14 C 0.9196(4) 0.7465(4) 0.7018(3) 0.0256(7) Uani 1 1 d . . .
H14 H 0.9740 0.7578 0.7598 0.031 Uiso 1 1 calc R . .
C15 C 0.9364(3) 0.8539(3) 0.6722(2) 0.0227(7) Uani 1 1 d . . .
C16 C 0.8541(3) 0.8364(3) 0.5866(2) 0.0219(7) Uani 1 1 d . . .
C17 C 0.7607(3) 0.7116(3) 0.5300(2) 0.0212(7) Uani 1 1 d . . .
H17 H 0.7080 0.7002 0.4711 0.025 Uiso 1 1 calc R . .
C18 C 1.1250(4) 0.9993(4) 0.8012(3) 0.0291(8) Uani 1 1 d . B .
H18A H 1.1592 0.9331 0.7842 0.035 Uiso 1 1 calc R . .
H18B H 1.0831 0.9881 0.8561 0.035 Uiso 1 1 calc R . .
C19 C 1.2356(4) 1.1380(4) 0.8280(3) 0.0328(9) Uani 1 1 d . . .
H19A H 1.3127 1.1474 0.8721 0.039 Uiso 0.264(13) 1 calc PR B 1
H19B H 1.2627 1.1565 0.7695 0.039 Uiso 0.264(13) 1 calc PR B 1
H19C H 1.2959 1.1547 0.8883 0.039 Uiso 0.736(13) 1 calc PR B 2
H19D H 1.2857 1.1402 0.7769 0.039 Uiso 0.736(13) 1 calc PR B 2
O2 O 1.1876(5) 1.2312(5) 0.8757(4) 0.0249(11) Uani 0.736(13) 1 d P B 1
C20 C 1.2880(6) 1.3637(6) 0.9107(5) 0.0316(15) Uani 0.736(13) 1 d P B 1
H20A H 1.3705 1.3648 0.9400 0.038 Uiso 0.736(13) 1 calc PR B 1
H20B H 1.2631 1.4164 0.9620 0.038 Uiso 0.736(13) 1 calc PR B 1
C21 C 1.3135(6) 1.4288(7) 0.8332(5) 0.0328(16) Uani 0.736(13) 1 d P B 1
H21A H 1.3934 1.5152 0.8588 0.039 Uiso 0.736(13) 1 calc PR B 1
H21B H 1.3275 1.3716 0.7775 0.039 Uiso 0.736(13) 1 calc PR B 1
O3 O 1.2042(7) 1.4476(8) 0.8043(5) 0.0318(14) Uani 0.736(13) 1 d P B 1
C22 C 1.2136(6) 1.5011(8) 0.7262(5) 0.0320(15) Uani 0.736(13) 1 d P B 1
H22A H 1.2101 1.4355 0.6667 0.038 Uiso 0.736(13) 1 calc PR B 1
H22B H 1.2980 1.5824 0.7421 0.038 Uiso 0.736(13) 1 calc PR B 1
C23 C 1.0988(6) 1.5333(6) 0.7108(5) 0.0301(15) Uani 0.736(13) 1 d PDU B 1
H23A H 1.0941 1.5862 0.7734 0.036 Uiso 0.736(13) 1 calc PR B 1
H23B H 1.1130 1.5875 0.6673 0.036 Uiso 0.736(13) 1 calc PR B 1
O2' O 1.2065(17) 1.2323(17) 0.8403(14) 0.036(4) Uani 0.264(13) 1 d PU B 2
C20' C 1.3162(19) 1.357(2) 0.8640(18) 0.045(5) Uani 0.264(13) 1 d PU B 2
H20C H 1.3746 1.3521 0.8195 0.055 Uiso 0.264(13) 1 calc PR B 2
H20D H 1.3667 1.3819 0.9304 0.055 Uiso 0.264(13) 1 calc PR B 2
C21' C 1.274(3) 1.468(2) 0.8575(17) 0.050(6) Uani 0.264(13) 1 d PU B 2
H21C H 1.2210 1.4787 0.9050 0.060 Uiso 0.264(13) 1 calc PR B 2
H21D H 1.3540 1.5543 0.8730 0.060 Uiso 0.264(13) 1 calc PR B 2
O3' O 1.204(2) 1.436(2) 0.7682(16) 0.044(5) Uani 0.264(13) 1 d PU B 2
C22' C 1.187(3) 1.539(3) 0.756(2) 0.059(7) Uani 0.264(13) 1 d PU B 2
H22C H 1.1343 1.5597 0.8009 0.070 Uiso 0.264(13) 1 calc PR B 2
H22D H 1.2748 1.6175 0.7755 0.070 Uiso 0.264(13) 1 calc PR B 2
C23' C 1.135(2) 1.527(3) 0.675(2) 0.082(9) Uani 0.264(13) 1 d PDU B 2
H23C H 1.1731 1.4901 0.6251 0.099 Uiso 0.264(13) 1 calc PR B 2
H23D H 1.1391 1.6114 0.6705 0.099 Uiso 0.264(13) 1 calc PR B 2
C24 C 0.9326(5) 1.3718(5) 0.5676(4) 0.0435(11) Uani 1 1 d D B .
H24A H 0.9941 1.3446 0.5364 0.052 Uiso 1 1 calc R . .
H24B H 0.9308 1.4460 0.5476 0.052 Uiso 1 1 calc R . .
C25 C 0.7959(4) 1.2561(4) 0.5358(3) 0.0339(9) Uani 1 1 d . . .
H25A H 0.7387 1.2806 0.5745 0.041 Uiso 1 1 calc R B .
H25B H 0.7594 1.2406 0.4675 0.041 Uiso 1 1 calc R . .
C26 C 0.8422(4) 1.0754(4) 0.4742(3) 0.0306(8) Uani 1 1 d . . .
H26A H 0.9391 1.1275 0.4887 0.037 Uiso 1 1 calc R B .
H26B H 0.8050 1.0723 0.4094 0.037 Uiso 1 1 calc R . .
C27 C 0.8066(4) 0.9382(4) 0.4761(3) 0.0286(8) Uani 1 1 d . B .
H27A H 0.7106 0.8890 0.4695 0.034 Uiso 1 1 calc R . .
H27B H 0.8315 0.8894 0.4223 0.034 Uiso 1 1 calc R . .
C28 C 0.2489(4) -0.1254(4) 0.2030(3) 0.0281(8) Uani 1 1 d . . .
H28A H 0.2943 -0.1721 0.2268 0.034 Uiso 1 1 calc R . .
H28B H 0.2489 -0.1397 0.1338 0.034 Uiso 1 1 calc R . .
C29 C 0.1101(4) -0.1819(4) 0.2141(3) 0.0367(9) Uani 1 1 d . . .
H29A H 0.1091 -0.1769 0.2821 0.044 Uiso 1 1 calc R . .
H29B H 0.0664 -0.1304 0.1961 0.044 Uiso 1 1 calc R . .
O1S O 0.5010(5) 1.0322(6) 0.9119(4) 0.0870(15) Uani 1 1 d . . .
C1S C 0.5588(8) 1.1375(8) 1.0103(6) 0.080(2) Uani 1 1 d . . .
H1SA H 0.6353 1.2158 1.0070 0.096 Uiso 1 1 calc R . .
H1SB H 0.4922 1.1661 1.0302 0.096 Uiso 1 1 calc R . .
C2S C 0.3992(8) 0.9142(9) 0.9180(6) 0.092(2) Uani 1 1 d . . .
H2SA H 0.3660 0.8448 0.8538 0.111 Uiso 1 1 calc R . .
H2SB H 0.3252 0.9324 0.9344 0.111 Uiso 1 1 calc R . .
O1W O 0.7949(4) 0.4415(4) 0.8616(3) 0.0631(11) Uani 1 1 d G . .
H1WA H 0.8530 0.5240 0.8887 0.095 Uiso 1 1 d G . .
H1WB H 0.7270 0.4375 0.8259 0.095 Uiso 1 1 d G . .
O2W O 0.6013(6) 0.9967(7) 0.2796(5) 0.0977(17) Uani 1 1 d G . .
H2WA H 0.5469 1.0048 0.3151 0.147 Uiso 1 1 d G . .
H2WB H 0.5667 0.9811 0.2197 0.147 Uiso 1 1 d G . .
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'
Br Br -0.2901 2.4595 '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
C15 O1 C18 116.1(3) . .
C24 O4 C23 115.9(4) . .
C24 O4 C23' 96.3(12) . .
C23 O4 C23' 23.7(11) . .
C25 O5 C26 112.8(3) . .
C16 O6 C27 117.2(3) . .
C1 N1 C9 120.4(3) . .
C1 N1 C28 118.3(3) . .
C9 N1 C28 121.3(3) . .
N1 C1 C2 122.3(3) . .
C1 C2 C3 121.5(4) . .
C2 C3 C4 117.1(3) . .
C2 C3 C10 121.5(3) . .
C4 C3 C10 121.4(3) . .
C5 C4 C9 117.3(3) . .
C5 C4 C3 122.9(3) . .
C9 C4 C3 119.8(3) . .
C6 C5 C4 121.1(4) . .
C5 C6 C7 120.7(4) . .
C8 C7 C6 120.5(4) . .
C7 C8 C9 119.9(4) . .
N1 C9 C8 120.8(3) . .
N1 C9 C4 118.7(3) . .
C8 C9 C4 120.5(3) . .
C11 C10 C3 123.7(3) . .
C10 C11 C12 127.2(3) . .
C13 C12 C17 118.4(3) . .
C13 C12 C11 118.1(3) . .
C17 C12 C11 123.5(3) . .
C14 C13 C12 121.9(3) . .
C15 C14 C13 119.1(3) . .
O1 C15 C14 124.9(3) . .
O1 C15 C16 115.0(3) . .
C14 C15 C16 120.1(3) . .
O6 C16 C17 125.1(3) . .
O6 C16 C15 114.5(3) . .
C17 C16 C15 120.4(3) . .
C16 C17 C12 120.1(3) . .
O1 C18 C19 107.4(3) . .
O2' C19 O2 23.2(9) . .
O2' C19 C18 118.1(9) . .
O2 C19 C18 107.8(4) . .
C20 O2 C19 112.0(5) . .
O2 C20 C21 113.3(5) . .
O3 C21 C20 108.4(6) . .
C21 O3 C22 113.3(6) . .
O3 C22 C23 107.9(6) . .
O4 C23 C22 111.0(5) . .
C19 O2' C20' 113.8(16) . .
O2' C20' C21' 112.0(18) . .
O3' C21' C20' 110(2) . .
C21' O3' C22' 111(3) . .
C23' C22' O3' 118(3) . .
C22' C23' O4 99(3) . .
O4 C24 C25 110.1(3) . .
O5 C25 C24 114.7(3) . .
O5 C26 C27 108.5(3) . .
O6 C27 C26 107.0(3) . .
N1 C28 C29 111.1(3) . .
N2 C29 C28 108.7(4) . .
C2S O1S C1S 109.9(6) . .
C2S C1S O1S 110.5(7) 2_677 .
O1S C2S C1S 113.9(7) . 2_677
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C15 1.363(4) .
O1 C18 1.446(4) .
O4 C24 1.424(7) .
O4 C23 1.431(6) .
O4 C23' 1.72(3) .
O5 C25 1.416(5) .
O5 C26 1.419(5) .
O6 C16 1.363(4) .
O6 C27 1.430(4) .
N2 C29 1.456(6) .
N1 C1 1.340(5) .
N1 C9 1.388(5) .
N1 C28 1.481(5) .
C1 C2 1.358(6) .
C2 C3 1.388(5) .
C3 C4 1.428(5) .
C3 C10 1.444(5) .
C4 C5 1.413(5) .
C4 C9 1.424(5) .
C5 C6 1.358(5) .
C6 C7 1.400(6) .
C7 C8 1.359(6) .
C8 C9 1.402(5) .
C10 C11 1.344(5) .
C11 C12 1.456(5) .
C12 C13 1.393(5) .
C12 C17 1.407(5) .
C13 C14 1.389(5) .
C14 C15 1.377(5) .
C15 C16 1.411(5) .
C16 C17 1.375(5) .
C18 C19 1.510(5) .
C19 O2' 1.250(18) .
C19 O2 1.467(7) .
O2 C20 1.414(7) .
C20 C21 1.514(9) .
C21 O3 1.397(11) .
O3 C22 1.435(8) .
C22 C23 1.517(10) .
O2' C20' 1.41(3) .
C20' C21' 1.57(4) .
C21' O3' 1.34(3) .
O3' C22' 1.35(4) .
C22' C23' 1.22(4) .
C24 C25 1.514(7) .
C26 C27 1.492(5) .
C28 C29 1.493(6) .
O1S C2S 1.427(9) .
O1S C1S 1.511(10) .
C1S C2S 1.474(11) 2_677
C2S C1S 1.474(11) 2_677
