#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:25:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180434 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/03/7210328.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_7210328
loop_
_publ_author_name
'Kobayashi, Yuhei'
'Tanaka, Yuki'
'Sato, Tomohiro'
'Fujiki, Michiya'
'Kuroda, Reiko'
'Imai, Yoshitane'
_publ_section_title
;
 Chiral anthracene fluorescence system using achiral 1-naphthylmethylamine
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              6259
_journal_paper_doi               10.1039/c3ce40765a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 115.801(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.589(2)
_cell_length_b                   5.9903(9)
_cell_length_c                   14.136(2)
_cell_measurement_reflns_used    1974
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      1974
_cell_measurement_theta_min      1.60
_cell_volume                     959.8(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      120(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8438
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.0191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                1974
_reflns_number_total             2419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40765a.txt
_cod_data_source_block           imai813_2
_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        959.7(3)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7210328
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
C1 C 0.5909(3) 0.5535(5) 0.2132(2) 0.0158(7) Uani 1 1 d .
H1 H 0.5885 0.4086 0.2396 0.019 Uiso 1 1 calc R
C2 C 0.6973(3) 0.6603(5) 0.2461(2) 0.0145(6) Uani 1 1 d .
C3 C 0.7018(3) 0.8776(5) 0.2057(2) 0.0165(7) Uani 1 1 d .
H3 H 0.7753 0.9530 0.2289 0.020 Uiso 1 1 calc R
C4 C 0.6018(3) 0.9768(5) 0.1343(2) 0.0165(7) Uani 1 1 d .
H4 H 0.6068 1.1192 0.1069 0.020 Uiso 1 1 calc R
C5 C 0.1673(3) 0.9648(6) -0.0757(2) 0.0220(7) Uani 1 1 d .
H5 H 0.1691 1.1045 -0.1068 0.026 Uiso 1 1 calc R
C6 C 0.0626(3) 0.8620(6) -0.1014(3) 0.0261(8) Uani 1 1 d .
H6 H -0.0082 0.9304 -0.1503 0.031 Uiso 1 1 calc R
C7 C 0.0571(3) 0.6528(7) -0.0562(3) 0.0258(8) Uani 1 1 d .
H7 H -0.0172 0.5838 -0.0743 0.031 Uiso 1 1 calc R
C8 C 0.1572(3) 0.5515(6) 0.0124(2) 0.0217(7) Uani 1 1 d .
H8 H 0.1523 0.4117 0.0420 0.026 Uiso 1 1 calc R
C9 C 0.3744(3) 0.5489(5) 0.1109(2) 0.0174(7) Uani 1 1 d .
H9 H 0.3711 0.4059 0.1385 0.021 Uiso 1 1 calc R
C10 C 0.3845(3) 0.9703(6) 0.0280(2) 0.0175(7) Uani 1 1 d .
H10 H 0.3880 1.1120 -0.0008 0.021 Uiso 1 1 calc R
C11 C 0.4884(2) 0.8703(5) 0.0995(2) 0.0149(6) Uani 1 1 d .
C12 C 0.4844(2) 0.6531(5) 0.1410(2) 0.0153(6) Uani 1 1 d .
C13 C 0.2698(3) 0.6515(6) 0.0411(2) 0.0194(7) Uani 1 1 d .
C14 C 0.2752(3) 0.8661(6) -0.0022(2) 0.0167(7) Uani 1 1 d .
C15 C 0.8070(3) 0.5469(5) 0.3250(2) 0.0183(7) Uani 1 1 d .
O16 O 0.80014(19) 0.3473(4) 0.34618(18) 0.0264(6) Uani 1 1 d .
O17 O 0.90079(17) 0.6649(4) 0.36592(15) 0.0188(5) Uani 1 1 d .
C21 C 1.1963(3) 0.2837(5) 0.4106(2) 0.0171(7) Uani 1 1 d .
C22 C 1.0965(3) 0.1521(6) 0.3739(2) 0.0194(7) Uani 1 1 d .
H22 H 1.0344 0.1878 0.3923 0.023 Uiso 1 1 calc R
C23 C 1.0851(3) -0.0348(6) 0.3094(2) 0.0251(8) Uani 1 1 d .
H23 H 1.0153 -0.1224 0.2844 0.030 Uiso 1 1 calc R
C24 C 1.1733(3) -0.0905(6) 0.2829(3) 0.0232(7) Uani 1 1 d .
H24 H 1.1652 -0.2183 0.2405 0.028 Uiso 1 1 calc R
C25 C 1.3704(3) -0.0143(6) 0.2904(2) 0.0230(8) Uani 1 1 d .
H25 H 1.3633 -0.1424 0.2485 0.028 Uiso 1 1 calc R
C26 C 1.4695(3) 0.1143(6) 0.3233(2) 0.0225(8) Uani 1 1 d .
H26 H 1.5311 0.0751 0.3047 0.027 Uiso 1 1 calc R
C27 C 1.4801(3) 0.3058(6) 0.3848(2) 0.0215(7) Uani 1 1 d .
H27 H 1.5482 0.3973 0.4060 0.026 Uiso 1 1 calc R
C28 C 1.3937(3) 0.3613(6) 0.4143(2) 0.0201(7) Uani 1 1 d .
H28 H 1.4033 0.4890 0.4571 0.024 Uiso 1 1 calc R
C29 C 1.2891(3) 0.2302(5) 0.3816(2) 0.0177(7) Uani 1 1 d .
C30 C 1.2775(3) 0.0405(6) 0.3180(2) 0.0178(7) Uani 1 1 d .
C31 C 1.2142(3) 0.4802(6) 0.4831(2) 0.0196(7) Uani 1 1 d .
H31A H 1.2878 0.4567 0.5480 0.024 Uiso 1 1 calc R
H31B H 1.2247 0.6166 0.4485 0.024 Uiso 1 1 calc R
N32 N 1.1157(2) 0.5178(4) 0.51258(19) 0.0166(6) Uani 1 1 d .
H32A H 1.0477 0.5418 0.4536 0.025 Uiso 1 1 calc R
H32B H 1.1320 0.6392 0.5554 0.025 Uiso 1 1 calc R
H32C H 1.1072 0.3956 0.5469 0.025 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 C12 121.8(3)
C1 C2 C3 119.5(3)
C1 C2 C15 119.1(3)
C3 C2 C15 121.5(3)
C4 C3 C2 120.5(3)
C3 C4 C11 121.3(3)
C6 C5 C14 120.9(3)
C5 C6 C7 120.8(3)
C8 C7 C6 120.3(3)
C7 C8 C13 121.0(3)
C13 C9 C12 121.4(3)
C11 C10 C14 121.2(3)
C10 C11 C12 119.8(3)
C10 C11 C4 122.3(3)
C12 C11 C4 117.8(3)
C9 C12 C1 122.0(3)
C9 C12 C11 118.8(3)
C1 C12 C11 119.1(3)
C9 C13 C8 122.1(3)
C9 C13 C14 119.3(3)
C8 C13 C14 118.7(3)
C10 C14 C5 122.3(3)
C10 C14 C13 119.5(3)
C5 C14 C13 118.2(3)
O16 C15 O17 124.7(3)
O16 C15 C2 118.3(3)
O17 C15 C2 117.0(3)
C22 C21 C29 119.1(3)
C22 C21 C31 122.9(3)
C29 C21 C31 117.9(3)
C21 C22 C23 121.1(3)
C24 C23 C22 120.5(3)
C23 C24 C30 120.6(3)
C26 C25 C30 121.0(3)
C25 C26 C27 119.7(3)
C28 C27 C26 120.9(3)
C27 C28 C29 120.9(3)
C30 C29 C28 118.2(3)
C30 C29 C21 119.3(3)
C28 C29 C21 122.5(3)
C29 C30 C24 119.3(3)
C29 C30 C25 119.3(3)
C24 C30 C25 121.4(3)
N32 C31 C21 114.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.370(4)
C1 C12 1.415(4)
C2 C3 1.433(4)
C2 C15 1.507(4)
C3 C4 1.361(4)
C4 C11 1.440(4)
C5 C6 1.353(4)
C5 C14 1.431(4)
C6 C7 1.422(5)
C7 C8 1.354(4)
C8 C13 1.426(4)
C9 C13 1.398(4)
C9 C12 1.405(4)
C10 C11 1.392(4)
C10 C14 1.398(4)
C11 C12 1.438(4)
C13 C14 1.438(5)
C15 O16 1.244(4)
C15 O17 1.279(4)
C21 C22 1.378(4)
C21 C29 1.434(4)
C21 C31 1.512(4)
C22 C23 1.411(5)
C23 C24 1.359(4)
C24 C30 1.420(4)
C25 C26 1.364(4)
C25 C30 1.422(4)
C26 C27 1.411(5)
C27 C28 1.363(4)
C28 C29 1.426(4)
C29 C30 1.416(4)
C31 N32 1.487(4)
