#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150975.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_7150975
loop_
_publ_author_name
'Imai, Yoshitane'
'Kamon, Kensaku'
'Murata, Katuzo'
'Harada, Takunori'
'Nakano, Yoko'
'Sato, Tomohiro'
'Fujiki, Michiya'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Preparation of a spontaneous resolution chiral fluorescent system
 using 2-anthracenecarboxylic acid
;
_journal_issue                   19
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3471
_journal_page_last               3475
_journal_paper_doi               10.1039/b808242a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C26 H27 N O2'
_chemical_formula_weight         385.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.5320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2494(14)
_cell_length_b                   6.5375(5)
_cell_length_c                   17.7953(13)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.84
_cell_measurement_theta_min      2.26
_cell_volume                     2093.8(3)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12454
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                3578
_reflns_number_total             4745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808242a.txt
_cod_data_source_block           imai85_3
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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
C1 C 0.74286(11) 0.0774(3) 0.52847(11) 0.0148(4) Uani 1 1 d . . .
H1 H 0.7538 -0.0408 0.5013 0.018 Uiso 1 1 calc R . .
C2 C 0.79244(11) 0.2355(3) 0.53782(10) 0.0137(4) Uani 1 1 d . . .
C3 C 0.77511(11) 0.4162(3) 0.57631(11) 0.0146(4) Uani 1 1 d . . .
H3 H 0.8086 0.5284 0.5812 0.018 Uiso 1 1 calc R . .
C4 C 0.71132(11) 0.4298(3) 0.60598(11) 0.0159(4) Uani 1 1 d . . .
H4 H 0.7010 0.5514 0.6315 0.019 Uiso 1 1 calc R . .
C5 C 0.48012(12) 0.1064(4) 0.66028(12) 0.0223(5) Uani 1 1 d . . .
H5 H 0.4694 0.2224 0.6887 0.027 Uiso 1 1 calc R . .
C6 C 0.43329(12) -0.0559(4) 0.65305(13) 0.0251(5) Uani 1 1 d . . .
H6 H 0.3903 -0.0523 0.6766 0.030 Uiso 1 1 calc R . .
C7 C 0.44765(12) -0.2315(4) 0.61064(13) 0.0245(5) Uani 1 1 d . . .
H7 H 0.4142 -0.3439 0.6060 0.029 Uiso 1 1 calc R . .
C8 C 0.50909(12) -0.2391(3) 0.57671(12) 0.0201(5) Uani 1 1 d . . .
H8 H 0.5180 -0.3570 0.5484 0.024 Uiso 1 1 calc R . .
C9 C 0.62477(11) -0.0775(3) 0.55026(11) 0.0162(4) Uani 1 1 d . . .
H9 H 0.6345 -0.1944 0.5218 0.019 Uiso 1 1 calc R . .
C10 C 0.59483(11) 0.2699(3) 0.63208(11) 0.0163(4) Uani 1 1 d . . .
H10 H 0.5842 0.3883 0.6593 0.020 Uiso 1 1 calc R . .
C11 C 0.54552(11) 0.1053(3) 0.62554(11) 0.0165(4) Uani 1 1 d . . .
C12 C 0.56055(11) -0.0721(3) 0.58307(11) 0.0170(5) Uani 1 1 d . . .
C13 C 0.67520(11) 0.0851(3) 0.55829(11) 0.0135(4) Uani 1 1 d . . .
C14 C 0.65954(11) 0.2649(3) 0.59944(11) 0.0145(4) Uani 1 1 d . . .
C15 C 0.86693(11) 0.2117(3) 0.51216(10) 0.0130(4) Uani 1 1 d . . .
O16 O 0.87919(8) 0.0522(2) 0.47757(8) 0.0167(3) Uani 1 1 d . . .
O17 O 0.91419(8) 0.3545(2) 0.52871(8) 0.0178(3) Uani 1 1 d . . .
C21 C 0.82914(11) -0.0887(3) 0.76261(10) 0.0132(4) Uani 1 1 d . . .
C22 C 0.85573(11) -0.2870(3) 0.75542(11) 0.0165(4) Uani 1 1 d . . .
H22 H 0.8355 -0.3966 0.7804 0.020 Uiso 1 1 calc R . .
C23 C 0.91089(11) -0.3275(3) 0.71272(11) 0.0181(5) Uani 1 1 d . . .
H23 H 0.9274 -0.4642 0.7085 0.022 Uiso 1 1 calc R . .
C24 C 0.94247(11) -0.1708(3) 0.67586(11) 0.0157(4) Uani 1 1 d . . .
C25 C 0.91678(11) 0.0262(3) 0.68326(11) 0.0171(5) Uani 1 1 d . . .
H25 H 0.9379 0.1359 0.6590 0.021 Uiso 1 1 calc R . .
C26 C 0.86088(11) 0.0668(3) 0.72531(10) 0.0157(4) Uani 1 1 d . . .
H26 H 0.8439 0.2034 0.7287 0.019 Uiso 1 1 calc R . .
C27 C 0.76706(11) -0.0492(3) 0.80940(11) 0.0148(4) Uani 1 1 d . . .
C28 C 0.78848(13) -0.1433(4) 0.88934(11) 0.0231(5) Uani 1 1 d . . .
H28A H 0.8348 -0.0811 0.9151 0.035 Uiso 1 1 calc R . .
H28B H 0.7955 -0.2911 0.8847 0.035 Uiso 1 1 calc R . .
H28C H 0.7488 -0.1177 0.9191 0.035 Uiso 1 1 calc R . .
C29 C 0.69531(12) -0.1497(4) 0.76901(12) 0.0218(5) Uani 1 1 d . . .
H29A H 0.6548 -0.1202 0.7973 0.033 Uiso 1 1 calc R . .
H29B H 0.7025 -0.2980 0.7668 0.033 Uiso 1 1 calc R . .
H29C H 0.6828 -0.0952 0.7172 0.033 Uiso 1 1 calc R . .
C30 C 0.75303(12) 0.1792(3) 0.81887(12) 0.0192(5) Uani 1 1 d . . .
H30A H 0.7161 0.1979 0.8525 0.029 Uiso 1 1 calc R . .
H30B H 0.7344 0.2397 0.7690 0.029 Uiso 1 1 calc R . .
H30C H 0.7996 0.2465 0.8412 0.029 Uiso 1 1 calc R . .
C31 C 1.00141(12) -0.2138(4) 0.62807(11) 0.0201(5) Uani 1 1 d . . .
H31A H 1.0352 -0.0947 0.6303 0.024 Uiso 1 1 calc R . .
H31B H 1.0311 -0.3334 0.6493 0.024 Uiso 1 1 calc R . .
N32 N 0.96879(9) -0.2558(3) 0.54702(9) 0.0153(4) Uani 1 1 d . . .
H32A H 0.9415 -0.3729 0.5443 0.023 Uiso 1 1 calc R . .
H32B H 1.0060 -0.2705 0.5191 0.023 Uiso 1 1 calc R . .
H32C H 0.9390 -0.1497 0.5282 0.023 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'
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
_geom_angle_publ_flag
C2 C1 C13 121.76(19) . . ?
C1 C2 C3 119.33(19) . . ?
C1 C2 C15 119.77(18) . . ?
C3 C2 C15 120.77(18) . . ?
C4 C3 C2 120.85(19) . . ?
C3 C4 C14 121.21(19) . . ?
C6 C5 C11 120.8(2) . . ?
C5 C6 C7 120.9(2) . . ?
C8 C7 C6 120.2(2) . . ?
C7 C8 C12 121.0(2) . . ?
C12 C9 C13 121.54(19) . . ?
C11 C10 C14 121.60(19) . . ?
C10 C11 C5 122.1(2) . . ?
C10 C11 C12 119.37(19) . . ?
C5 C11 C12 118.50(19) . . ?
C9 C12 C8 122.2(2) . . ?
C9 C12 C11 119.23(19) . . ?
C8 C12 C11 118.53(19) . . ?
C9 C13 C1 122.17(19) . . ?
C9 C13 C14 119.39(18) . . ?
C1 C13 C14 118.43(18) . . ?
C10 C14 C4 122.82(19) . . ?
C10 C14 C13 118.84(19) . . ?
C4 C14 C13 118.34(18) . . ?
O16 C15 O17 123.81(19) . . ?
O16 C15 C2 118.53(18) . . ?
O17 C15 C2 117.64(18) . . ?
C26 C21 C22 117.11(18) . . ?
C26 C21 C27 122.59(18) . . ?
C22 C21 C27 120.29(18) . . ?
C23 C22 C21 121.53(19) . . ?
C22 C23 C24 120.9(2) . . ?
C25 C24 C23 117.83(19) . . ?
C25 C24 C31 120.84(19) . . ?
C23 C24 C31 121.3(2) . . ?
C24 C25 C26 121.34(19) . . ?
C25 C26 C21 121.3(2) . . ?
C30 C27 C29 108.95(18) . . ?
C30 C27 C21 112.10(17) . . ?
C29 C27 C21 108.85(16) . . ?
C30 C27 C28 108.06(17) . . ?
C29 C27 C28 109.16(17) . . ?
C21 C27 C28 109.67(17) . . ?
N32 C31 C24 111.89(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.365(3) . ?
C1 C13 1.423(3) . ?
C2 C3 1.427(3) . ?
C2 C15 1.512(3) . ?
C3 C4 1.359(3) . ?
C4 C14 1.425(3) . ?
C5 C6 1.355(3) . ?
C5 C11 1.432(3) . ?
C6 C7 1.422(3) . ?
C7 C8 1.359(3) . ?
C8 C12 1.432(3) . ?
C9 C12 1.394(3) . ?
C9 C13 1.398(3) . ?
C10 C11 1.395(3) . ?
C10 C14 1.400(3) . ?
C11 C12 1.435(3) . ?
C13 C14 1.439(3) . ?
C15 O16 1.250(2) . ?
C15 O17 1.272(2) . ?
C21 C26 1.392(3) . ?
C21 C22 1.398(3) . ?
C21 C27 1.535(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.392(3) . ?
C24 C25 1.385(3) . ?
C24 C31 1.504(3) . ?
C25 C26 1.387(3) . ?
C27 C30 1.529(3) . ?
C27 C29 1.533(3) . ?
C27 C28 1.540(3) . ?
C31 N32 1.492(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653433
2 PubChem 139190322
