#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/36/4103654.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_4103654
loop_
_publ_author_name
'Yasuhiro Ishida'
'Ammathnadu S. Achalkumar'
'Shun-ya Kato'
'Yukiko Kai'
'Aya Misawa'
'Yumi Hayashi'
'Kuniyo Yamada'
'Yuki Matsuoka'
'Motoo Shiro'
'Kazuhiko Saigo'
_publ_section_title
;
 Tunable Chiral Reaction Media Based on Two-Component Liquid Crystals:
 Regio-, Diastereo-, and Enantiocontrolled Photodimerization of
 Anthracenecarboxylic Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17435
_journal_page_last               17446
_journal_paper_doi               10.1021/ja105221u
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C29 H30 N O4, C8 H7 O3, C2 H6 O '
_chemical_formula_sum            'C39 H43 N O8'
_chemical_formula_weight         653.77
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.8081(3)
_cell_length_b                   12.9504(5)
_cell_length_c                   45.9633(20)
_cell_measurement_reflns_used    15137
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.4
_cell_measurement_theta_min      3.4
_cell_volume                     3457.2(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (R/MSC, Rigaku, 2005)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (R/MSC, Rigaku, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla, 2003)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.126
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            34544
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. '
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     447
_refine_ls_number_reflns         3557
_refine_ls_R_factor_gt           0.0997
_refine_ls_shift/su_max          0.0080
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1807P)²+1.2964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2928
_reflns_number_gt                2504
_reflns_number_total             3557
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja105221u_si_001.cif
_cod_data_source_block           (R)-11_(S)-mandelic_acid_EtOH
_cod_original_formula_sum        'C39 H43 N O8 '
_cod_database_code               4103654
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-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
O(1) O -0.0318(11) 0.2828(3) 0.28372(11) 0.0596(13) Uani 1.00 1 d .
O(2) O 0.5009(11) 0.4328(3) 0.38900(10) 0.0618(14) Uani 1.00 1 d .
O(3) O 0.2495(10) 0.2955(3) 0.41724(9) 0.0583(13) Uani 1.00 1 d .
O(4) O -0.0951(11) 0.1960(4) 0.39275(11) 0.0665(15) Uani 1.00 1 d .
O(5) O -0.3725(11) 0.0834(3) 0.22117(11) 0.0637(14) Uani 1.00 1 d .
O(6) O -0.5257(11) 0.3357(3) 0.24699(10) 0.0611(13) Uani 1.00 1 d .
O(7) O -0.7214(11) 0.1888(3) 0.24689(11) 0.0663(15) Uani 1.00 1 d .
O(8) O 0.2236(10) 0.4911(3) 0.22825(11) 0.0637(14) Uani 1.00 1 d .
N(1) N -0.1799(14) 0.4756(4) 0.26415(13) 0.0649(18) Uani 1.00 1 d .
C(1) C 0.1097(16) 0.3524(5) 0.33030(15) 0.060(2) Uani 1.00 1 d .
C(2) C 0.2855(16) 0.4059(5) 0.34375(15) 0.0582(19) Uani 1.00 1 d .
C(3) C 0.3310(15) 0.3886(5) 0.37334(15) 0.0553(18) Uani 1.00 1 d .
C(4) C 0.1995(15) 0.3152(5) 0.38872(14) 0.0542(18) Uani 1.00 1 d .
C(5) C 0.0156(15) 0.2647(5) 0.37505(15) 0.0565(18) Uani 1.00 1 d .
C(6) C -0.0282(14) 0.2812(5) 0.34581(15) 0.0527(17) Uani 1.00 1 d .
C(7) C 0.0562(15) 0.3721(5) 0.29798(14) 0.0553(19) Uani 1.00 1 d .
C(8) C -0.1198(17) 0.4585(5) 0.29478(14) 0.061(2) Uani 1.00 1 d .
C(9) C 0.6318(18) 0.5135(5) 0.37620(16) 0.065(2) Uani 1.00 1 d .
C(10) C 0.7825(16) 0.5619(5) 0.39944(15) 0.0559(18) Uani 1.00 1 d .
C(11) C 0.9915(18) 0.6074(5) 0.39158(16) 0.060(2) Uani 1.00 1 d .
C(12) C 1.1334(17) 0.6498(6) 0.41260(16) 0.0622(19) Uani 1.00 1 d .
C(13) C 1.0682(15) 0.6504(5) 0.44114(18) 0.061(2) Uani 1.00 1 d .
C(14) C 0.8519(17) 0.6084(6) 0.44942(18) 0.063(2) Uani 1.00 1 d .
C(15) C 0.7185(18) 0.5635(5) 0.42834(16) 0.063(2) Uani 1.00 1 d .
C(16) C 0.1750(18) 0.3715(5) 0.43754(15) 0.063(2) Uani 1.00 1 d .
C(17) C 0.3249(16) 0.3745(5) 0.46383(16) 0.0575(19) Uani 1.00 1 d .
C(18) C 0.5411(18) 0.3242(5) 0.46426(16) 0.065(2) Uani 1.00 1 d .
C(19) C 0.6742(18) 0.3275(6) 0.48917(17) 0.065(2) Uani 1.00 1 d .
C(20) C 0.6015(18) 0.3795(6) 0.51346(19) 0.070(2) Uani 1.00 1 d .
C(21) C 0.3930(18) 0.4297(6) 0.51348(19) 0.072(2) Uani 1.00 1 d .
C(22) C 0.2571(18) 0.4263(6) 0.48877(16) 0.065(2) Uani 1.00 1 d .
C(23) C -0.2878(17) 0.1418(6) 0.38073(16) 0.064(2) Uani 1.00 1 d .
C(24) C -0.3407(16) 0.0534(5) 0.40045(16) 0.0577(18) Uani 1.00 1 d .
C(25) C -0.1844(18) -0.0279(5) 0.40333(17) 0.064(2) Uani 1.00 1 d .
C(26) C -0.237(2) -0.1136(5) 0.42024(15) 0.070(2) Uani 1.00 1 d .
C(27) C -0.4394(18) -0.1174(5) 0.43566(17) 0.064(2) Uani 1.00 1 d .
C(28) C -0.5948(18) -0.0381(5) 0.43339(16) 0.065(2) Uani 1.00 1 d .
C(29) C -0.5506(17) 0.0488(5) 0.41580(17) 0.066(2) Uani 1.00 1 d .
C(30) C -0.3327(15) 0.2395(5) 0.19446(14) 0.0552(18) Uani 1.00 1 d .
C(31) C -0.1453(18) 0.2954(8) 0.18561(17) 0.080(2) Uani 1.00 1 d .
C(32) C -0.140(2) 0.3416(9) 0.15837(19) 0.095(3) Uani 1.00 1 d .
C(33) C -0.323(2) 0.3351(6) 0.14004(17) 0.073(2) Uani 1.00 1 d .
C(34) C -0.513(2) 0.2778(6) 0.14775(17) 0.074(2) Uani 1.00 1 d .
C(35) C -0.5167(19) 0.2297(6) 0.17500(17) 0.071(2) Uani 1.00 1 d .
C(36) C -0.3453(17) 0.1920(5) 0.22418(15) 0.0598(19) Uani 1.00 1 d .
C(37) C -0.5436(16) 0.2424(6) 0.24091(16) 0.0582(19) Uani 1.00 1 d .
C(38) C 0.267(2) 0.5262(8) 0.1996(2) 0.080(2) Uani 1.00 1 d .
C(39) C 0.512(2) 0.5536(11) 0.1936(2) 0.111(4) Uani 1.00 1 d .
H(1) H 0.3751 0.4540 0.3330 0.070 Uiso 1.00 1 c R
H(1A) H -0.0573 0.4643 0.2544 0.078 Uiso 1.00 1 c R
H(1B) H -0.2081 0.5386 0.2606 0.078 Uiso 1.00 1 c R
H(1C) H -0.2791 0.4330 0.2575 0.078 Uiso 1.00 1 c R
H(1O) H -0.1649 0.2951 0.2775 0.071 Uiso 1.00 1 c R
H(2) H -0.1492 0.2452 0.3363 0.063 Uiso 1.00 1 c R
H(3) H 0.2016 0.3935 0.2880 0.066 Uiso 1.00 1 c R
H(4) H -0.2604 0.4405 0.3058 0.073 Uiso 1.00 1 c R
H(5) H -0.0560 0.5230 0.3031 0.073 Uiso 1.00 1 c R
H(5O) H -0.3536 0.0549 0.2374 0.076 Uiso 1.00 1 c R
H(6) H 0.5275 0.5662 0.3678 0.078 Uiso 1.00 1 c R
H(7) H 0.7288 0.4855 0.3603 0.078 Uiso 1.00 1 c R
H(8) H 1.0364 0.6092 0.3717 0.072 Uiso 1.00 1 c R
H(8O) H 0.3189 0.4448 0.2326 0.076 Uiso 1.00 1 c R
H(9) H 1.2773 0.6788 0.4071 0.075 Uiso 1.00 1 c R
H(10) H 1.1676 0.6788 0.4555 0.073 Uiso 1.00 1 c R
H(11) H 0.8011 0.6114 0.4691 0.076 Uiso 1.00 1 c R
H(12) H 0.5769 0.5324 0.4338 0.075 Uiso 1.00 1 c R
H(13) H 0.0148 0.3562 0.4435 0.075 Uiso 1.00 1 c R
H(14) H 0.1761 0.4401 0.4280 0.075 Uiso 1.00 1 c R
H(15) H 0.5944 0.2884 0.4475 0.078 Uiso 1.00 1 c R
H(16) H 0.8186 0.2930 0.4895 0.078 Uiso 1.00 1 c R
H(17) H 0.6957 0.3810 0.5303 0.084 Uiso 1.00 1 c R
H(18) H 0.3428 0.4662 0.5302 0.086 Uiso 1.00 1 c R
H(19) H 0.1125 0.4605 0.4889 0.078 Uiso 1.00 1 c R
H(20) H -0.2501 0.1162 0.3610 0.077 Uiso 1.00 1 c R
H(21) H -0.4225 0.1883 0.3793 0.077 Uiso 1.00 1 c R
H(22) H -0.0401 -0.0245 0.3936 0.077 Uiso 1.00 1 c R
H(23) H -0.1331 -0.1700 0.4211 0.084 Uiso 1.00 1 c R
H(24) H -0.4714 -0.1747 0.4479 0.077 Uiso 1.00 1 c R
H(25) H -0.7355 -0.0419 0.4439 0.078 Uiso 1.00 1 c R
H(26) H -0.6599 0.1031 0.4143 0.079 Uiso 1.00 1 c R
H(27) H -0.0170 0.3026 0.1983 0.096 Uiso 1.00 1 c R
H(28) H -0.0065 0.3784 0.1525 0.114 Uiso 1.00 1 c R
H(29) H -0.3197 0.3701 0.1219 0.088 Uiso 1.00 1 c R
H(30) H -0.6390 0.2710 0.1348 0.089 Uiso 1.00 1 c R
H(31) H -0.6469 0.1897 0.1804 0.085 Uiso 1.00 1 c R
H(32) H -0.1979 0.2062 0.2347 0.072 Uiso 1.00 1 c R
H(33) H 0.1698 0.5877 0.1959 0.096 Uiso 1.00 1 c R
H(34) H 0.2184 0.4717 0.1858 0.096 Uiso 1.00 1 c R
H(35) H 0.5491 0.6197 0.2029 0.133 Uiso 1.00 1 c R
H(36) H 0.5357 0.5594 0.1725 0.133 Uiso 1.00 1 c R
H(37) H 0.6133 0.4996 0.2014 0.133 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, 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_publ_flag
C(3) O(2) C(9) 118.9(5) yes
C(4) O(3) C(16) 115.8(5) yes
C(5) O(4) C(23) 117.2(5) yes
C(2) C(1) C(6) 121.4(6) yes
C(2) C(1) C(7) 119.9(6) yes
C(6) C(1) C(7) 118.7(7) yes
C(1) C(2) C(3) 119.6(7) yes
O(2) C(3) C(2) 126.0(7) yes
O(2) C(3) C(4) 114.5(6) yes
C(2) C(3) C(4) 119.4(7) yes
O(3) C(4) C(3) 119.4(6) yes
O(3) C(4) C(5) 120.3(6) yes
C(3) C(4) C(5) 120.2(6) yes
O(4) C(5) C(4) 113.3(6) yes
O(4) C(5) C(6) 126.3(7) yes
C(4) C(5) C(6) 120.2(7) yes
C(1) C(6) C(5) 119.1(7) yes
O(1) C(7) C(1) 112.5(5) yes
O(1) C(7) C(8) 108.1(6) yes
C(1) C(7) C(8) 110.5(5) yes
N(1) C(8) C(7) 111.3(5) yes
O(2) C(9) C(10) 108.8(5) yes
C(9) C(10) C(11) 119.6(6) yes
C(9) C(10) C(15) 121.9(8) yes
C(11) C(10) C(15) 118.5(7) yes
C(10) C(11) C(12) 120.3(7) yes
C(11) C(12) C(13) 120.5(8) yes
C(12) C(13) C(14) 120.0(8) yes
C(13) C(14) C(15) 118.2(7) yes
C(10) C(15) C(14) 122.3(8) yes
O(3) C(16) C(17) 111.8(7) yes
C(16) C(17) C(18) 121.2(6) yes
C(16) C(17) C(22) 121.2(8) yes
C(18) C(17) C(22) 117.6(7) yes
C(17) C(18) C(19) 119.6(7) yes
C(18) C(19) C(20) 121.2(9) yes
C(19) C(20) C(21) 120.3(8) yes
C(20) C(21) C(22) 119.1(8) yes
C(17) C(22) C(21) 122.2(9) yes
O(4) C(23) C(24) 107.6(6) yes
C(23) C(24) C(25) 120.1(8) yes
C(23) C(24) C(29) 121.0(7) yes
C(25) C(24) C(29) 118.9(7) yes
C(24) C(25) C(26) 120.7(9) yes
C(25) C(26) C(27) 120.5(8) yes
C(26) C(27) C(28) 119.8(7) yes
C(27) C(28) C(29) 121.4(8) yes
C(24) C(29) C(28) 118.6(8) yes
C(31) C(30) C(35) 117.7(6) yes
C(31) C(30) C(36) 121.7(7) yes
C(35) C(30) C(36) 120.6(7) yes
C(30) C(31) C(32) 120.9(9) yes
C(31) C(32) C(33) 121.0(11) yes
C(32) C(33) C(34) 120.0(8) yes
C(33) C(34) C(35) 119.0(9) yes
C(30) C(35) C(34) 121.3(9) yes
O(5) C(36) C(30) 108.8(5) yes
O(5) C(36) C(37) 112.8(6) yes
C(30) C(36) C(37) 108.6(6) yes
O(6) C(37) O(7) 123.3(7) yes
O(6) C(37) C(36) 117.6(7) yes
O(7) C(37) C(36) 119.0(6) yes
O(8) C(38) C(39) 114.7(8) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(7) 1.424(8) yes
O(2) C(3) 1.349(9) yes
O(2) C(9) 1.419(10) yes
O(3) C(4) 1.367(7) yes
O(3) C(16) 1.423(8) yes
O(4) C(5) 1.366(9) yes
O(4) C(23) 1.432(11) yes
O(5) C(36) 1.422(8) yes
O(6) C(37) 1.245(9) yes
O(7) C(37) 1.274(10) yes
O(8) C(38) 1.413(10) yes
N(1) C(8) 1.467(9) yes
C(1) C(2) 1.380(12) yes
C(1) C(6) 1.415(10) yes
C(1) C(7) 1.539(9) yes
C(2) C(3) 1.403(9) yes
C(3) C(4) 1.410(10) yes
C(4) C(5) 1.402(11) yes
C(5) C(6) 1.384(9) yes
C(7) C(8) 1.523(11) yes
C(9) C(10) 1.517(11) yes
C(10) C(11) 1.397(13) yes
C(10) C(15) 1.380(10) yes
C(11) C(12) 1.384(12) yes
C(12) C(13) 1.365(11) yes
C(13) C(14) 1.421(13) yes
C(14) C(15) 1.370(12) yes
C(16) C(17) 1.490(11) yes
C(17) C(18) 1.414(13) yes
C(17) C(22) 1.385(10) yes
C(18) C(19) 1.382(12) yes
C(19) C(20) 1.371(12) yes
C(20) C(21) 1.374(14) yes
C(21) C(22) 1.384(12) yes
C(23) C(24) 1.492(10) yes
C(24) C(25) 1.396(12) yes
C(24) C(29) 1.410(13) yes
C(25) C(26) 1.390(10) yes
C(26) C(27) 1.371(14) yes
C(27) C(28) 1.371(12) yes
C(28) C(29) 1.409(10) yes
C(30) C(31) 1.369(13) yes
C(30) C(35) 1.399(12) yes
C(30) C(36) 1.500(9) yes
C(31) C(32) 1.388(12) yes
C(32) C(33) 1.358(16) yes
C(33) C(34) 1.375(15) yes
C(34) C(35) 1.399(11) yes
C(36) C(37) 1.531(12) yes
C(38) C(39) 1.497(19) yes
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_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O(1) H(1O) O(6) . 3.399(8) 0.840 2.576 166.8 no
O(1) H(1O) N(1) . 2.790(7) 0.840 2.418 107.6 no
O(5) H(5O) O(8) 3_545 2.753(7) 0.840 1.935 164.5 no
O(8) H(8O) O(6) 1_655 2.629(7) 0.840 1.802 167.5 no
N(1) H(1A) O(8) . 2.873(9) 0.855 2.055 160.0 no
N(1) H(1B) O(7) 3_455 2.865(8) 0.848 2.017 178.5 no
N(1) H(1C) O(6) . 2.817(9) 0.854 1.968 172.9 no
