#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151311.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_7151311
loop_
_publ_author_name
'Adams, Harry'
'Bawa, Ramadan A.'
'Jones, Simon'
_publ_section_title
;
 N-Alkyl oxazolidines as stereocontrol elements in asymmetric
 Diels?Alder cycloadditions of 9-substituted anthracene derivatives
;
_journal_issue                   22
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              4206
_journal_paper_doi               10.1039/b610055d
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C25 H23 N O'
_chemical_formula_weight         353.44
_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                 121.240(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.188(3)
_cell_length_b                   7.0490(10)
_cell_length_c                   17.257(2)
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.701
_cell_measurement_theta_min      4.479
_cell_volume                     1891.7(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker smart1000'
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10741
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.2084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                1903
_reflns_number_total             2328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b610055d.txt
_cod_data_source_block           osj8m
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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      C2
_cod_database_code               7151311
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89484(10) 0.3665(2) 0.85808(10) 0.0331(4) Uani 1 1 d . . .
N3 N 0.84135(11) 0.6398(3) 0.77812(12) 0.0259(4) Uani 1 1 d . . .
C1 C 1.02020(13) 0.4193(3) 0.72813(15) 0.0267(5) Uani 1 1 d . . .
H1 H 1.0348 0.5092 0.7749 0.032 Uiso 1 1 calc R . .
C2 C 1.07813(14) 0.3786(4) 0.70296(15) 0.0303(5) Uani 1 1 d . . .
H2 H 1.1316 0.4438 0.7313 0.036 Uiso 1 1 calc R . .
C3 C 1.06062(15) 0.2421(4) 0.63582(16) 0.0330(6) Uani 1 1 d . . .
H3 H 1.1030 0.2114 0.6214 0.040 Uiso 1 1 calc R . .
C4 C 0.98351(14) 0.1557(4) 0.59233(15) 0.0293(5) Uani 1 1 d . . .
H4 H 0.9719 0.0641 0.5470 0.035 Uiso 1 1 calc R . .
C5 C 0.68715(14) 0.0959(3) 0.52238(15) 0.0288(5) Uani 1 1 d . . .
H5 H 0.6745 0.0200 0.4714 0.035 Uiso 1 1 calc R . .
C6 C 0.62437(14) 0.1344(4) 0.53975(16) 0.0322(5) Uani 1 1 d . . .
H6 H 0.5680 0.0861 0.5011 0.039 Uiso 1 1 calc R . .
C7 C 0.64278(14) 0.2472(3) 0.61581(16) 0.0309(5) Uani 1 1 d . . .
H7 H 0.5984 0.2726 0.6280 0.037 Uiso 1 1 calc R . .
C8 C 0.72271(14) 0.3195(3) 0.67166(15) 0.0267(5) Uani 1 1 d . . .
H8 H 0.7334 0.3934 0.7225 0.032 Uiso 1 1 calc R . .
C9 C 0.87455(13) 0.3641(3) 0.70825(13) 0.0211(4) Uani 1 1 d . . .
C10 C 0.83658(13) 0.1216(3) 0.56220(14) 0.0229(5) Uani 1 1 d . . .
H10 H 0.8244 0.0354 0.5146 0.028 Uiso 1 1 calc R . .
C11 C 0.93746(13) 0.3289(3) 0.68535(14) 0.0208(4) Uani 1 1 d . . .
C12 C 0.91849(13) 0.1987(3) 0.61297(14) 0.0224(5) Uani 1 1 d . . .
C13 C 0.77224(13) 0.1676(3) 0.57942(14) 0.0222(4) Uani 1 1 d . . .
C14 C 0.79117(13) 0.2857(3) 0.65500(14) 0.0213(4) Uani 1 1 d . . .
C15 C 0.80499(14) 0.8172(3) 0.87876(15) 0.0296(5) Uani 1 1 d . . .
H15A H 0.7969 0.9357 0.8444 0.035 Uiso 1 1 calc R . .
H15B H 0.7487 0.7522 0.8514 0.035 Uiso 1 1 calc R . .
C16 C 0.8480(2) 0.7932(4) 0.72562(18) 0.0436(7) Uani 1 1 d . . .
H16A H 0.8292 0.7478 0.6644 0.065 Uiso 1 1 calc R . .
H16B H 0.9079 0.8359 0.7551 0.065 Uiso 1 1 calc R . .
H16C H 0.8114 0.8991 0.7220 0.065 Uiso 1 1 calc R . .
C2A C 0.89777(14) 0.4812(3) 0.79145(14) 0.0245(5) Uani 1 1 d . . .
H2A H 0.9576 0.5304 0.8176 0.029 Uiso 1 1 calc R . .
C4A C 0.86870(14) 0.6900(3) 0.87168(14) 0.0253(5) Uani 1 1 d . . .
H4A H 0.9263 0.7530 0.9013 0.030 Uiso 1 1 calc R . .
C5A C 0.87747(15) 0.4928(3) 0.91230(15) 0.0278(5) Uani 1 1 d . . .
H5A1 H 0.9252 0.4900 0.9763 0.033 Uiso 1 1 calc R . .
H5A2 H 0.8237 0.4559 0.9096 0.033 Uiso 1 1 calc R . .
C1B C 0.83595(13) 0.8654(3) 0.97626(14) 0.0255(5) Uani 1 1 d . . .
C2B C 0.89784(14) 1.0068(4) 1.01996(16) 0.0320(5) Uani 1 1 d . . .
H2B H 0.9181 1.0754 0.9873 0.038 Uiso 1 1 calc R . .
C3B C 0.92978(17) 1.0480(4) 1.11000(18) 0.0428(7) Uani 1 1 d . . .
H3B H 0.9721 1.1440 1.1392 0.051 Uiso 1 1 calc R . .
C4B C 0.90026(17) 0.9497(4) 1.15790(17) 0.0449(7) Uani 1 1 d . . .
H4B H 0.9223 0.9777 1.2200 0.054 Uiso 1 1 calc R . .
C5B C 0.83858(17) 0.8104(4) 1.11496(17) 0.0384(6) Uani 1 1 d . . .
H5B H 0.8181 0.7427 1.1477 0.046 Uiso 1 1 calc R . .
C6B C 0.80640(14) 0.7688(4) 1.02461(16) 0.0321(6) Uani 1 1 d . . .
H6B H 0.7638 0.6733 0.9956 0.039 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O1 C5A 106.59(17) . . ?
C2A N3 C16 112.97(18) . . ?
C2A N3 C4A 101.72(16) . . ?
C16 N3 C4A 114.60(18) . . ?
C2 C1 C11 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C12 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C12 C4 H4 119.3 . . ?
C6 C5 C13 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C13 C5 H5 119.5 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C14 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C14 C8 H8 119.5 . . ?
C11 C9 C14 120.03(19) . . ?
C11 C9 C2A 119.53(18) . . ?
C14 C9 C2A 120.42(18) . . ?
C13 C10 C12 121.4(2) . . ?
C13 C10 H10 119.3 . . ?
C12 C10 H10 119.3 . . ?
C9 C11 C1 124.27(19) . . ?
C9 C11 C12 119.33(18) . . ?
C1 C11 C12 116.37(18) . . ?
C10 C12 C4 120.9(2) . . ?
C10 C12 C11 119.52(19) . . ?
C4 C12 C11 119.5(2) . . ?
C10 C13 C5 120.2(2) . . ?
C10 C13 C14 120.03(18) . . ?
C5 C13 C14 119.78(19) . . ?
C9 C14 C13 119.28(18) . . ?
C9 C14 C8 123.63(19) . . ?
C13 C14 C8 117.09(19) . . ?
C1B C15 C4A 111.28(18) . . ?
C1B C15 H15A 109.4 . . ?
C4A C15 H15A 109.4 . . ?
C1B C15 H15B 109.4 . . ?
C4A C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C2A N3 104.17(16) . . ?
O1 C2A C9 110.24(18) . . ?
N3 C2A C9 116.28(17) . . ?
O1 C2A H2A 108.6 . . ?
N3 C2A H2A 108.6 . . ?
C9 C2A H2A 108.6 . . ?
N3 C4A C15 113.20(17) . . ?
N3 C4A C5A 100.41(17) . . ?
C15 C4A C5A 113.75(18) . . ?
N3 C4A H4A 109.7 . . ?
C15 C4A H4A 109.7 . . ?
C5A C4A H4A 109.7 . . ?
O1 C5A C4A 105.67(16) . . ?
O1 C5A H5A1 110.6 . . ?
C4A C5A H5A1 110.6 . . ?
O1 C5A H5A2 110.6 . . ?
C4A C5A H5A2 110.6 . . ?
H5A1 C5A H5A2 108.7 . . ?
C6B C1B C2B 118.8(2) . . ?
C6B C1B C15 121.6(2) . . ?
C2B C1B C15 119.5(2) . . ?
C3B C2B C1B 120.6(2) . . ?
C3B C2B H2B 119.7 . . ?
C1B C2B H2B 119.7 . . ?
C2B C3B C4B 120.1(2) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B C5B 119.6(2) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C4B C5B C6B 120.4(2) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C5B C6B C1B 120.4(2) . . ?
C5B C6B H6B 119.8 . . ?
C1B C6B H6B 119.8 . . ?
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
O1 C2A 1.429(3) . ?
O1 C5A 1.440(3) . ?
N3 C2A 1.453(3) . ?
N3 C16 1.455(3) . ?
N3 C4A 1.465(3) . ?
C1 C2 1.362(3) . ?
C1 C11 1.436(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.410(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.345(3) . ?
C3 H3 0.9500 . ?
C4 C12 1.433(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.350(3) . ?
C5 C13 1.428(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.418(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.360(3) . ?
C7 H7 0.9500 . ?
C8 C14 1.435(3) . ?
C8 H8 0.9500 . ?
C9 C11 1.413(3) . ?
C9 C14 1.416(3) . ?
C9 C2A 1.514(3) . ?
C10 C13 1.387(3) . ?
C10 C12 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.440(3) . ?
C13 C14 1.431(3) . ?
C15 C1B 1.510(3) . ?
C15 C4A 1.519(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C2A H2A 1.0000 . ?
C4A C5A 1.528(3) . ?
C4A H4A 1.0000 . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C1B C6B 1.383(3) . ?
C1B C2B 1.396(3) . ?
C2B C3B 1.378(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.383(4) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.382(4) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.383(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -1.9(3) . . . . ?
C1 C2 C3 C4 3.1(3) . . . . ?
C2 C3 C4 C12 -0.2(3) . . . . ?
C13 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C14 0.6(3) . . . . ?
C14 C9 C11 C1 172.3(2) . . . . ?
C2A C9 C11 C1 -9.4(3) . . . . ?
C14 C9 C11 C12 -5.9(3) . . . . ?
C2A C9 C11 C12 172.43(18) . . . . ?
C2 C1 C11 C9 179.8(2) . . . . ?
C2 C1 C11 C12 -1.9(3) . . . . ?
C13 C10 C12 C4 -177.63(19) . . . . ?
C13 C10 C12 C11 0.2(3) . . . . ?
C3 C4 C12 C10 174.1(2) . . . . ?
C3 C4 C12 C11 -3.7(3) . . . . ?
C9 C11 C12 C10 5.1(3) . . . . ?
C1 C11 C12 C10 -173.21(19) . . . . ?
C9 C11 C12 C4 -177.03(19) . . . . ?
C1 C11 C12 C4 4.6(3) . . . . ?
C12 C10 C13 C5 175.9(2) . . . . ?
C12 C10 C13 C14 -4.7(3) . . . . ?
C6 C5 C13 C10 177.9(2) . . . . ?
C6 C5 C13 C14 -1.5(3) . . . . ?
C11 C9 C14 C13 1.4(3) . . . . ?
C2A C9 C14 C13 -176.84(18) . . . . ?
C11 C9 C14 C8 -177.84(19) . . . . ?
C2A C9 C14 C8 3.9(3) . . . . ?
C10 C13 C14 C9 3.9(3) . . . . ?
C5 C13 C14 C9 -176.7(2) . . . . ?
C10 C13 C14 C8 -176.80(19) . . . . ?
C5 C13 C14 C8 2.6(3) . . . . ?
C7 C8 C14 C9 177.1(2) . . . . ?
C7 C8 C14 C13 -2.2(3) . . . . ?
C5A O1 C2A N3 -28.4(2) . . . . ?
C5A O1 C2A C9 -153.84(17) . . . . ?
C16 N3 C2A O1 168.74(18) . . . . ?
C4A N3 C2A O1 45.39(19) . . . . ?
C16 N3 C2A C9 -69.8(2) . . . . ?
C4A N3 C2A C9 166.90(18) . . . . ?
C11 C9 C2A O1 -113.8(2) . . . . ?
C14 C9 C2A O1 64.5(2) . . . . ?
C11 C9 C2A N3 128.0(2) . . . . ?
C14 C9 C2A N3 -53.7(3) . . . . ?
C2A N3 C4A C15 -164.40(18) . . . . ?
C16 N3 C4A C15 73.4(2) . . . . ?
C2A N3 C4A C5A -42.8(2) . . . . ?
C16 N3 C4A C5A -165.0(2) . . . . ?
C1B C15 C4A N3 -179.89(18) . . . . ?
C1B C15 C4A C5A 66.3(2) . . . . ?
C2A O1 C5A C4A 1.0(2) . . . . ?
N3 C4A C5A O1 26.1(2) . . . . ?
C15 C4A C5A O1 147.29(17) . . . . ?
C4A C15 C1B C6B -98.6(2) . . . . ?
C4A C15 C1B C2B 79.4(3) . . . . ?
C6B C1B C2B C3B 0.8(3) . . . . ?
C15 C1B C2B C3B -177.3(2) . . . . ?
C1B C2B C3B C4B -0.3(4) . . . . ?
C2B C3B C4B C5B -0.1(4) . . . . ?
C3B C4B C5B C6B 0.1(4) . . . . ?
C4B C5B C6B C1B 0.4(4) . . . . ?
C2B C1B C6B C5B -0.8(3) . . . . ?
C15 C1B C6B C5B 177.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10163758
2 PubChem 11991291
