#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:54:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180454 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/23/7212318.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_7212318
loop_
_publ_author_name
'Imai, Yoshitane'
'Murata, Katuzo'
'Nakano, Yoko'
'Harada, Takunori'
'Kinuta, Takafumi'
'Tajima, Nobuo'
'Sato, Tomohiro'
'Fujiki, Michiya'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Control of solid-state chiral optical properties of a chiral
 supramolecular organic fluorophore consisting of 1-pyrenesulfonic acid
 and chiral amine molecules
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1688
_journal_paper_doi               10.1039/b924760m
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H23 N O3 S'
_chemical_formula_weight         453.53
_chemical_name_systematic
;
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 91.676(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.575(2)
_cell_length_b                   5.5363(5)
_cell_length_c                   18.7917(19)
_cell_measurement_reflns_used    3812
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      1.98
_cell_volume                     2139.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω 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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6689
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9217
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4430
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0490
_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)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                3812
_reflns_number_total             4430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b924760m.txt
_cod_data_source_block           Nimai814_1
_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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2139.7(4)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7212318
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'
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
C1 C 0.92141(12) 0.9775(5) 0.80875(13) 0.0167(6) Uani 1 1 d .
C2 C 0.95005(12) 0.8182(5) 0.76220(14) 0.0177(6) Uani 1 1 d .
H2 H 0.9766 0.6909 0.7805 0.021 Uiso 1 1 calc R
C3 C 0.94041(12) 0.8423(5) 0.68936(14) 0.0199(6) Uani 1 1 d .
H3 H 0.9602 0.7304 0.6584 0.024 Uiso 1 1 calc R
C4 C 0.90239(13) 1.0271(5) 0.66090(14) 0.0183(6) Uani 1 1 d .
C5 C 0.83136(12) 1.3792(5) 0.67942(13) 0.0163(6) Uani 1 1 d .
C6 C 0.80110(13) 1.5449(5) 0.72558(15) 0.0181(6) Uani 1 1 d .
C7 C 0.81194(13) 1.5190(5) 0.80027(15) 0.0193(6) Uani 1 1 d .
H7 H 0.7924 1.6307 0.8315 0.023 Uiso 1 1 calc R
C8 C 0.84936(13) 1.3395(5) 0.82786(14) 0.0179(6) Uani 1 1 d .
H8 H 0.8548 1.3260 0.8781 0.021 Uiso 1 1 calc R
C9 C 0.88112(12) 1.1680(5) 0.78293(14) 0.0152(6) Uani 1 1 d .
C10 C 0.87143(12) 1.1920(5) 0.70816(14) 0.0165(6) Uani 1 1 d .
C11 C 0.89277(14) 1.0622(5) 0.58579(15) 0.0238(7) Uani 1 1 d .
H11 H 0.9141 0.9573 0.5540 0.029 Uiso 1 1 calc R
C12 C 0.85469(13) 1.2380(6) 0.55881(14) 0.0238(7) Uani 1 1 d .
H12 H 0.8494 1.2534 0.5086 0.029 Uiso 1 1 calc R
C13 C 0.82175(12) 1.4035(5) 0.60420(14) 0.0197(6) Uani 1 1 d .
C14 C 0.78194(14) 1.5885(6) 0.57786(16) 0.0250(7) Uani 1 1 d .
H14 H 0.7750 1.6050 0.5279 0.030 Uiso 1 1 calc R
C15 C 0.75248(13) 1.7481(6) 0.62319(16) 0.0255(7) Uani 1 1 d .
H15 H 0.7253 1.8721 0.6040 0.031 Uiso 1 1 calc R
C16 C 0.76204(13) 1.7298(5) 0.69598(16) 0.0226(6) Uani 1 1 d .
H16 H 0.7421 1.8432 0.7264 0.027 Uiso 1 1 calc R
S1 S 0.93979(3) 0.94485(13) 0.90121(3) 0.01791(15) Uani 1 1 d .
O1 O 0.96725(9) 1.1762(4) 0.92346(10) 0.0223(5) Uani 1 1 d .
O2 O 0.98639(10) 0.7486(4) 0.90665(11) 0.0269(5) Uani 1 1 d .
O3 O 0.87945(8) 0.8900(3) 0.93668(9) 0.0224(5) Uani 1 1 d .
C21 C 0.58932(13) -0.1699(5) 0.79601(14) 0.0201(6) Uani 1 1 d .
H21 H 0.5662 -0.3154 0.8041 0.024 Uiso 1 1 calc R
C22 C 0.62161(11) -0.0601(6) 0.85148(13) 0.0180(5) Uani 1 1 d .
C23 C 0.65496(14) 0.1588(5) 0.83960(16) 0.0234(6) Uani 1 1 d .
H23 H 0.6772 0.2366 0.8782 0.028 Uiso 1 1 calc R
C24 C 0.65555(13) 0.2592(6) 0.77385(15) 0.0237(6) Uani 1 1 d .
H24 H 0.6777 0.4078 0.7672 0.028 Uiso 1 1 calc R
C25 C 0.62555(14) 0.2444(6) 0.64530(16) 0.0275(7) Uani 1 1 d .
H25 H 0.6485 0.3902 0.6371 0.033 Uiso 1 1 calc R
C26 C 0.59406(14) 0.1289(6) 0.58984(16) 0.0286(7) Uani 1 1 d .
H26 H 0.5954 0.1950 0.5432 0.034 Uiso 1 1 calc R
C27 C 0.55986(13) -0.0862(7) 0.60120(15) 0.0287(7) Uani 1 1 d .
H27 H 0.5380 -0.1640 0.5623 0.034 Uiso 1 1 calc R
C28 C 0.55770(13) -0.1845(6) 0.66761(15) 0.0250(7) Uani 1 1 d .
H28 H 0.5346 -0.3307 0.6747 0.030 Uiso 1 1 calc R
C29 C 0.58964(11) -0.0703(6) 0.72591(13) 0.0189(5) Uani 1 1 d .
C30 C 0.62384(13) 0.1465(5) 0.71501(15) 0.0204(6) Uani 1 1 d .
C31 C 0.62176(12) -0.1745(5) 0.92450(13) 0.0192(6) Uani 1 1 d .
H31 H 0.6002 -0.3358 0.9199 0.023 Uiso 1 1 calc R
C32 C 0.68923(13) -0.2136(6) 0.95760(15) 0.0269(7) Uani 1 1 d .
H32A H 0.7154 -0.3085 0.9250 0.040 Uiso 1 1 calc R
H32B H 0.6856 -0.3007 1.0027 0.040 Uiso 1 1 calc R
H32C H 0.7101 -0.0569 0.9664 0.040 Uiso 1 1 calc R
N33 N 0.58250(10) -0.0232(4) 0.97414(11) 0.0179(5) Uani 1 1 d .
H33A H 0.6077 0.0984 0.9923 0.027 Uiso 1 1 calc R
H33B H 0.5684 -0.1171 1.0103 0.027 Uiso 1 1 calc R
H33C H 0.5477 0.0406 0.9498 0.027 Uiso 1 1 calc R
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
C2 C1 C9 120.8(2)
C2 C1 S1 118.0(2)
C9 C1 S1 121.1(2)
C3 C2 C1 120.8(2)
C2 C3 C4 121.1(3)
C3 C4 C11 122.7(2)
C3 C4 C10 119.1(2)
C11 C4 C10 118.2(3)
C6 C5 C10 119.9(2)
C6 C5 C13 119.6(2)
C10 C5 C13 120.4(2)
C16 C6 C5 119.0(2)
C16 C6 C7 122.4(3)
C5 C6 C7 118.6(2)
C8 C7 C6 121.6(3)
C7 C8 C9 121.6(2)
C1 C9 C10 118.2(2)
C1 C9 C8 124.1(2)
C10 C9 C8 117.8(2)
C9 C10 C5 120.5(2)
C9 C10 C4 120.0(2)
C5 C10 C4 119.5(2)
C12 C11 C4 122.3(3)
C11 C12 C13 121.3(3)
C14 C13 C5 118.9(3)
C14 C13 C12 122.7(2)
C5 C13 C12 118.3(2)
C15 C14 C13 121.0(3)
C14 C15 C16 120.9(3)
C15 C16 C6 120.6(3)
O2 S1 O1 112.85(12)
O2 S1 O3 112.45(12)
O1 S1 O3 112.35(12)
O2 S1 C1 105.46(13)
O1 S1 C1 105.12(12)
O3 S1 C1 107.98(11)
C22 C21 C29 121.2(3)
C21 C22 C23 119.3(3)
C21 C22 C31 119.7(3)
C23 C22 C31 121.0(2)
C24 C23 C22 120.9(3)
C23 C24 C30 121.1(3)
C26 C25 C30 120.0(3)
C25 C26 C27 120.6(3)
C28 C27 C26 120.6(3)
C27 C28 C29 120.3(3)
C30 C29 C28 119.5(3)
C30 C29 C21 118.6(2)
C28 C29 C21 121.9(3)
C29 C30 C24 118.9(2)
C29 C30 C25 119.0(3)
C24 C30 C25 122.0(3)
N33 C31 C22 110.0(2)
N33 C31 C32 109.0(2)
C22 C31 C32 114.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.386(4)
C1 C9 1.418(4)
C1 S1 1.777(3)
C2 C3 1.384(4)
C3 C4 1.386(4)
C4 C11 1.433(4)
C4 C10 1.436(4)
C5 C6 1.419(4)
C5 C10 1.421(4)
C5 C13 1.428(3)
C6 C16 1.406(4)
C6 C7 1.422(4)
C7 C8 1.352(4)
C8 C9 1.440(4)
C9 C10 1.420(3)
C11 C12 1.340(4)
C12 C13 1.435(4)
C13 C14 1.393(4)
C14 C15 1.380(4)
C15 C16 1.380(4)
S1 O2 1.451(2)
S1 O1 1.456(2)
S1 O3 1.4580(19)
C21 C22 1.363(4)
C21 C29 1.428(4)
C22 C23 1.414(4)
C22 C31 1.511(4)
C23 C24 1.355(4)
C24 C30 1.413(4)
C25 C26 1.370(4)
C25 C30 1.419(4)
C26 C27 1.402(5)
C27 C28 1.364(4)
C28 C29 1.411(4)
C29 C30 1.409(4)
C31 N33 1.506(3)
C31 C32 1.520(3)
