#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:06:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178458 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/79/4027944.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_4027944
loop_
_publ_author_name
'Jan Vávra'
'Lukáš Severa'
'Ivana Císařová'
'Blanka Klepetářová'
'David Šaman'
'Dušan Koval'
'Václav Kašička'
'Filip Teplý'
_publ_section_title
;
 Search for Conglomerate in Set of [7]Helquat Salts: Multigram Resolution
 of Helicene-Viologen Hybrid by Preferential Crystallization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1329
_journal_page_last               1342
_journal_paper_doi               10.1021/jo301615k
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C30 H26 N2, 2(H O4 S), H2 O'
_chemical_formula_sum            'C30 H30 N2 O9 S2'
_chemical_formula_weight         626.71
_space_group_IT_number           142
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4bd 2c'
_symmetry_space_group_name_H-M   'I 41/a c d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-12-14
_audit_creation_method           CRYSTALS_ver_14.05
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.9753(16)
_cell_length_b                   19.9753(16)
_cell_length_c                   27.812(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    170
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     11097(2)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            23511
_diffrn_reflns_theta_full        76.504
_diffrn_reflns_theta_max         79.692
_diffrn_reflns_theta_min         4.427
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.269
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             5248
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9496
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.0081384
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 16.1 19.2 13.5 3.83 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1275
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0935
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                2130
_reflns_number_total             2961
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   5.29
_oxford_diffrn_Wilson_scale      0.85
_oxford_refine_ls_r_factor_ref   0.0698
_oxford_refine_ls_scale          1.010(5)
_oxford_reflns_number_all        2961
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_oxford_structure_analysis_title 'RED_NOABS in I4(1)/acd'
_cod_data_source_file            jo301615k_2_H2PO4.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'I 41/a c d '
_cod_database_code               4027944
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
x+1/2,y,-z+1/2
-x+1/2,-y,z+1/2
x+1,y+1/2,-z+1
-x+1,-y+1/2,z+1
-y+1/4,-x+1/4,-z+1/4
y+1/4,x+1/4,z+1/4
-y+3/4,-x+3/4,-z+3/4
y+3/4,x+3/4,z+3/4
y+3/4,-x+1/4,-z+3/4
-y+3/4,x+1/4,z+3/4
y+5/4,-x+3/4,-z+5/4
-y+5/4,x+3/4,z+5/4
-y+1/4,-x+3/4,z+3/4
y+1/4,x+3/4,-z+3/4
-y+3/4,-x+5/4,z+5/4
y+3/4,x+5/4,-z+5/4
x,-y,-z+1/2
-x,y,z+1/2
x+1/2,-y+1/2,-z+1
-x+1/2,y+1/2,z+1
y+1/4,-x+1/4,z+3/4
-y+1/4,x+1/4,-z+3/4
y+3/4,-x+3/4,z+5/4
-y+3/4,x+3/4,-z+5/4
-x+1/2,y,-z
x+1/2,-y,z
-x+1,y+1/2,-z+1/2
x+1,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
C1 C 0.30785(14) 0.53324(14) 0.40563(9) 0.0453 1.0000 Uani .
N2 N 0.35356(13) 0.58248(13) 0.40314(8) 0.0516 1.0000 Uani .
C3 C 0.3385(2) 0.64741(17) 0.41409(12) 0.0637 1.0000 Uani .
C4 C 0.2774(2) 0.66425(16) 0.42897(13) 0.0642 1.0000 Uani .
C5 C 0.22894(17) 0.61487(15) 0.43786(10) 0.0540 1.0000 Uani .
C6 C 0.16551(19) 0.63006(19) 0.45785(12) 0.0645 1.0000 Uani .
C7 C 0.12213(18) 0.5798(2) 0.46879(12) 0.0690 1.0000 Uani .
C8 C 0.13983(17) 0.5130(2) 0.46198(11) 0.0608 1.0000 Uani .
C9 C 0.20023(15) 0.49605(16) 0.44203(9) 0.0517 1.0000 Uani .
C10 C 0.24550(14) 0.54722(14) 0.42806(9) 0.0458 1.0000 Uani .
C11 C 0.42315(16) 0.56601(18) 0.38866(14) 0.0623 1.0000 Uani .
C12 C 0.44178(16) 0.50023(19) 0.41070(11) 0.0593 1.0000 Uani .
C13 C 0.39423(14) 0.44732(17) 0.39315(10) 0.0501 1.0000 Uani .
C14 C 0.32799(14) 0.46745(14) 0.38661(9) 0.0452 1.0000 Uani .
C15 C 0.41454(16) 0.38204(17) 0.38313(10) 0.0551 1.0000 Uani .
C16 C 0.4869(2) 0.3624(2) 0.38903(16) 0.0773 1.0000 Uani .
S17 S 0.42390(6) 0.68298(5) 0.27805(3) 0.0726 1.0000 Uani .
O18 O 0.3706(2) 0.72840(18) 0.27069(15) 0.1114 1.0000 Uani .
O19 O 0.4001(2) 0.61474(17) 0.27986(14) 0.1008 1.0000 Uani .
O20 O 0.4606(2) 0.69673(18) 0.32387(12) 0.1023 1.0000 Uani .
O21 O 0.47385(18) 0.68870(19) 0.23854(11) 0.0946 1.0000 Uani .
O22 O 0.2578(7) 0.2019(5) -0.0195(3) 0.1478 0.5000 Uani .
H91 H 0.2122 0.4512 0.4379 0.0625 1.0000 Uiso R
H81 H 0.1102 0.4803 0.4710 0.0728 1.0000 Uiso R
H61 H 0.1542 0.6746 0.4632 0.0767 1.0000 Uiso R
H41 H 0.2668 0.7090 0.4341 0.0768 1.0000 Uiso R
H31 H 0.3721 0.6793 0.4119 0.0759 1.0000 Uiso R
H162 H 0.5014 0.3359 0.3625 0.1162 1.0000 Uiso R
H163 H 0.4931 0.3385 0.4183 0.1163 1.0000 Uiso R
H161 H 0.5146 0.4005 0.3904 0.1165 1.0000 Uiso R
H122 H 0.4388 0.5054 0.4462 0.0715 1.0000 Uiso R
H121 H 0.4861 0.4887 0.4016 0.0717 1.0000 Uiso R
H112 H 0.4522 0.6012 0.4010 0.0747 1.0000 Uiso R
H111 H 0.4257 0.5644 0.3537 0.0739 1.0000 Uiso R
H71 H 0.0798 0.5894 0.4809 0.0830 1.0000 Uiso R
H201 H 0.4863 0.7295 0.3202 0.1539 0.5000 Uiso R
H211 H 0.4926 0.7250 0.2414 0.1421 0.5000 Uiso R
H221 H 0.2990 0.1840 -0.0056 0.2279 0.5000 Uiso R
H222 H 0.2433 0.1665 -0.0328 0.2279 0.5000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 . C1 C10 . 118.3(3) yes
N2 . C1 C14 . 116.7(2) yes
C10 . C1 C14 . 124.9(3) yes
C1 . N2 C3 . 122.3(3) yes
C1 . N2 C11 . 119.2(3) yes
C3 . N2 C11 . 118.5(3) yes
N2 . C3 C4 . 120.8(3) yes
N2 . C3 H31 . 118.5 no
C4 . C3 H31 . 120.7 no
C3 . C4 C5 . 120.6(3) yes
C3 . C4 H41 . 120.0 no
C5 . C4 H41 . 119.3 no
C4 . C5 C6 . 122.4(3) yes
C4 . C5 C10 . 118.3(3) yes
C6 . C5 C10 . 119.2(3) yes
C5 . C6 C7 . 119.9(3) yes
C5 . C6 H61 . 119.1 no
C7 . C6 H61 . 121.0 no
C6 . C7 C8 . 121.0(3) yes
C6 . C7 H71 . 120.4 no
C8 . C7 H71 . 118.6 no
C7 . C8 C9 . 121.0(4) yes
C7 . C8 H81 . 118.8 no
C9 . C8 H81 . 120.1 no
C8 . C9 C10 . 119.6(3) yes
C8 . C9 H91 . 120.8 no
C10 . C9 H91 . 119.6 no
C1 . C10 C9 . 122.5(3) yes
C1 . C10 C5 . 118.4(3) yes
C9 . C10 C5 . 119.0(3) yes
N2 . C11 C12 . 108.4(3) yes
N2 . C11 H112 . 107.6 no
C12 . C11 H112 . 109.9 no
N2 . C11 H111 . 109.1 no
C12 . C11 H111 . 111.5 no
H112 . C11 H111 . 110.2 no
C11 . C12 C13 . 109.1(3) yes
C11 . C12 H122 . 107.5 no
C13 . C12 H122 . 110.9 no
C11 . C12 H121 . 109.6 no
C13 . C12 H121 . 109.5 no
H122 . C12 H121 . 110.2 no
C12 . C13 C14 . 116.1(3) yes
C12 . C13 C15 . 122.6(3) yes
C14 . C13 C15 . 121.3(3) yes
C1 . C14 C14 11_555 123.55(16) yes
C1 . C14 C13 . 118.0(3) yes
C14 11_555 C14 C13 . 118.41(18) yes
C13 . C15 C15 11_555 119.73(19) yes
C13 . C15 C16 . 120.1(3) yes
C15 11_555 C15 C16 . 120.2(2) yes
C15 . C16 H162 . 110.6 no
C15 . C16 H163 . 110.5 no
H162 . C16 H163 . 110.2 no
C15 . C16 H161 . 110.9 no
H162 . C16 H161 . 107.5 no
H163 . C16 H161 . 107.0 no
O18 . S17 O19 . 111.3(3) yes
O18 . S17 O20 . 112.0(2) yes
O19 . S17 O20 . 107.8(2) yes
O18 . S17 O21 . 110.4(2) yes
O19 . S17 O21 . 108.6(2) yes
O20 . S17 O21 . 106.6(2) yes
S17 . O20 H201 . 109.8 no
S17 . O21 H211 . 107.6 no
O22 29_555 O22 H221 . 81.5 no
O22 29_555 O22 H222 . 109.0 no
H221 . O22 H222 . 98.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.344(4) yes
C1 C10 . 1.421(4) yes
C1 C14 . 1.473(4) yes
N2 C3 . 1.366(4) yes
N2 C11 . 1.484(4) yes
C3 C4 . 1.331(6) yes
C3 H31 . 0.927 no
C4 C5 . 1.404(5) yes
C4 H41 . 0.930 no
C5 C6 . 1.416(5) yes
C5 C10 . 1.418(4) yes
C6 C7 . 1.361(6) yes
C6 H61 . 0.930 no
C7 C8 . 1.392(6) yes
C7 H71 . 0.931 no
C8 C9 . 1.371(4) yes
C8 H81 . 0.918 no
C9 C10 . 1.419(4) yes
C9 H91 . 0.933 no
C11 C12 . 1.497(5) yes
C11 H112 . 0.975 no
C11 H111 . 0.975 no
C12 C13 . 1.502(5) yes
C12 H122 . 0.993 no
C12 H121 . 0.949 no
C13 C14 . 1.395(4) yes
C13 C15 . 1.394(5) yes
C14 C14 11_555 1.437(6) yes
C15 C15 11_555 1.392(7) yes
C15 C16 . 1.506(5) yes
C16 H162 . 0.954 no
C16 H163 . 0.951 no
C16 H161 . 0.942 no
S17 O18 . 1.414(4) yes
S17 O19 . 1.444(4) yes
S17 O20 . 1.495(4) yes
S17 O21 . 1.489(3) yes
O20 H201 . 0.838 no
O21 H211 . 0.821 no
O22 O22 29_555 1.129(19) yes
O22 H221 . 0.978 no
O22 H222 . 0.849 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 H41 O22 6_565 154 0.93 2.25 3.113(5) yes
C16 H163 O21 27_454 147 0.95 2.56 3.398(5) yes
C11 H111 O19 . 148 0.98 2.34 3.212(5) yes
C7 H71 O18 10_455 172 0.93 2.39 3.315(5) yes
O20 H201 O20 8_564 169 0.84 1.82 2.647(5) yes
O21 H211 O21 8_564 170 0.82 1.85 2.662(5) yes
O22 H221 O19 12_444 169 0.98 1.78 2.743(5) yes
