#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:25:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180261 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/47/7114765.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_7114765
loop_
_publ_author_name
'Bach, Thorsten'
'Aechtner, Tobias'
'Neumüller, Bernhard'
_publ_section_title
;
 Intermolecular hydrogen binding of a chiral host and a prochiral
 imidazolidinone: enantioselective Norrish--Yang cyclisation in solution
;
_journal_issue                   7
_journal_name_full               'Chemical Communications'
_journal_page_first              607
_journal_paper_doi               10.1039/b100300n
_journal_year                    2001
_chemical_formula_sum            'C21 H22 N2 O4'
_chemical_formula_weight         366.41
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.946(1)
_cell_length_b                   12.500(1)
_cell_length_c                   16.350(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      38.0
_cell_measurement_theta_min      20.0
_cell_volume                     1828.3(3)
_computing_cell_refinement       'EXPRESS (Enraf-Nonius)'
_computing_data_collection       'EXPRESS (Enraf-Nonius)'
_computing_data_reduction        'XCAD4 (Univ. of Marburg)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1996)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997) PLATON-98 (Spek, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CAD4 (Enraf-Nonius)'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3696
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         4.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  '7200 s'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '9 psi-scans'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(18)
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    'free refinement'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0628P)²+0.2170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                3209
_reflns_number_total             3399
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b100300n.txt
_cod_data_source_block           kaep6
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7114765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
O1 O -0.28026(14) 0.81648(11) 0.12244(8) 0.0364(3) Uani 1 1 d
H1 H -0.285(4) 0.882(3) 0.130(2) 0.106(13) Uiso 1 1 d
O2 O 0.33125(12) 0.73836(11) 0.15333(7) 0.0367(3) Uani 1 1 d
O3 O 0.11986(14) 0.58932(10) 0.35106(8) 0.0378(3) Uani 1 1 d
O4 O 0.39733(13) 0.52105(9) 0.34225(8) 0.0339(3) Uani 1 1 d
N1 N 0.11587(15) 0.83846(11) 0.15727(9) 0.0314(3) Uani 1 1 d
N2 N 0.14133(15) 0.70989(11) 0.25016(8) 0.0285(3) Uani 1 1 d
C1 C -0.12727(18) 0.79052(13) 0.11285(10) 0.0289(3) Uani 1 1 d
C11 C -0.11802(19) 0.67058(13) 0.09831(9) 0.0285(3) Uani 1 1 d
C12 C -0.2282(2) 0.60364(15) 0.13044(12) 0.0384(4) Uani 1 1 d
H121 H -0.310(2) 0.6334(17) 0.1576(13) 0.034(5) Uiso 1 1 d
C13 C -0.2198(3) 0.49354(16) 0.11954(12) 0.0458(5) Uani 1 1 d
H131 H -0.297(3) 0.4503(19) 0.1447(15) 0.052(6) Uiso 1 1 d
C14 C -0.1019(3) 0.44943(15) 0.07750(12) 0.0444(5) Uani 1 1 d
H141 H -0.095(3) 0.372(2) 0.0636(19) 0.074(8) Uiso 1 1 d
C15 C 0.0081(2) 0.51481(17) 0.04593(13) 0.0466(5) Uani 1 1 d
H151 H 0.090(3) 0.4876(18) 0.0136(15) 0.053(6) Uiso 1 1 d
C16 C -0.0002(2) 0.62482(15) 0.05675(11) 0.0366(4) Uani 1 1 d
H161 H 0.073(3) 0.671(2) 0.0300(15) 0.056(7) Uiso 1 1 d
C2 C -0.0509(2) 0.85754(15) 0.04505(11) 0.0359(4) Uani 1 1 d
H21 H -0.059(2) 0.8177(18) -0.0086(14) 0.043(6) Uiso 1 1 d
H22 H -0.110(3) 0.9258(19) 0.0413(13) 0.049(6) Uiso 1 1 d
C3 C 0.1120(2) 0.87595(16) 0.07188(12) 0.0392(4) Uani 1 1 d
H31 H 0.188(2) 0.8341(18) 0.0414(13) 0.040(5) Uiso 1 1 d
H32 H 0.140(3) 0.954(2) 0.0663(17) 0.062(7) Uiso 1 1 d
C4 C -0.03415(19) 0.82460(13) 0.18950(10) 0.0296(3) Uani 1 1 d
H41 H -0.073(2) 0.8914(16) 0.2086(12) 0.031(5) Uiso 1 1 d
C5 C -0.01386(18) 0.74594(14) 0.26059(10) 0.0300(3) Uani 1 1 d
H51 H -0.023(2) 0.7790(15) 0.3133(12) 0.029(5) Uiso 1 1 d
H52 H -0.087(2) 0.6847(17) 0.2594(12) 0.035(5) Uiso 1 1 d
C6 C 0.21069(17) 0.76032(13) 0.18263(9) 0.0283(3) Uani 1 1 d
C7 C 0.20036(18) 0.63498(13) 0.30259(10) 0.0277(3) Uani 1 1 d
C8 C 0.36950(18) 0.61984(13) 0.30153(10) 0.0283(3) Uani 1 1 d
H81 H 0.406(2) 0.6177(16) 0.2455(12) 0.027(4) Uiso 1 1 d
C81 C 0.44392(17) 0.71260(12) 0.34589(10) 0.0285(3) Uani 1 1 d
C82 C 0.4080(2) 0.73311(14) 0.42786(11) 0.0371(4) Uani 1 1 d
H821 H 0.328(2) 0.6905(17) 0.4530(13) 0.039(5) Uiso 1 1 d
C83 C 0.4814(3) 0.81394(17) 0.46991(13) 0.0489(5) Uani 1 1 d
H831 H 0.456(3) 0.830(2) 0.5280(17) 0.064(7) Uiso 1 1 d
C84 C 0.5887(2) 0.87439(18) 0.43104(16) 0.0535(6) Uani 1 1 d
H841 H 0.640(3) 0.934(2) 0.4608(16) 0.064(8) Uiso 1 1 d
C85 C 0.6230(2) 0.85611(16) 0.34981(15) 0.0493(5) Uani 1 1 d
H851 H 0.702(3) 0.899(2) 0.3195(18) 0.070(8) Uiso 1 1 d
C86 C 0.55054(19) 0.77530(14) 0.30696(13) 0.0368(4) Uani 1 1 d
H861 H 0.577(2) 0.7615(17) 0.2509(14) 0.041(5) Uiso 1 1 d
C9 C 0.5512(2) 0.49109(16) 0.33764(15) 0.0412(4) Uani 1 1 d
H91 H 0.562(3) 0.418(2) 0.3628(14) 0.050(6) Uiso 1 1 d
H92 H 0.619(3) 0.545(2) 0.3687(14) 0.052(6) Uiso 1 1 d
H93 H 0.580(3) 0.490(2) 0.2828(17) 0.054(7) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8 O4 C9 111.77(13)
C6 N1 C4 112.37(13)
C6 N1 C3 122.19(15)
C4 N1 C3 111.09(13)
C7 N2 C6 128.43(13)
C7 N2 C5 119.95(13)
C6 N2 C5 111.61(13)
O1 C1 C11 107.23(14)
O1 C1 C2 112.46(14)
C11 C1 C2 113.44(14)
O1 C1 C4 111.33(13)
C11 C1 C4 111.40(13)
C2 C1 C4 101.02(13)
C16 C11 C12 118.48(16)
C16 C11 C1 121.86(16)
C12 C11 C1 119.61(16)
C13 C12 C11 120.51(18)
C14 C13 C12 120.17(19)
C13 C14 C15 119.80(17)
C14 C15 C16 120.08(18)
C11 C16 C15 120.97(18)
C3 C2 C1 107.13(14)
N1 C3 C2 104.18(14)
N1 C4 C5 104.01(13)
N1 C4 C1 103.54(13)
C5 C4 C1 119.72(14)
N2 C5 C4 102.74(13)
O2 C6 N1 126.73(15)
O2 C6 N2 126.72(15)
N1 C6 N2 106.54(13)
O3 C7 N2 119.98(15)
O3 C7 C8 122.54(15)
N2 C7 C8 117.29(14)
O4 C8 C81 111.18(13)
O4 C8 C7 106.00(13)
C81 C8 C7 109.53(13)
C86 C81 C82 119.50(16)
C86 C81 C8 120.81(15)
C82 C81 C8 119.66(16)
C83 C82 C81 119.89(19)
C84 C83 C82 120.1(2)
C83 C84 C85 120.50(19)
C84 C85 C86 120.1(2)
C81 C86 C85 119.97(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.415(2)
O2 C6 1.212(2)
O3 C7 1.213(2)
O4 C8 1.425(2)
O4 C9 1.429(2)
N1 C6 1.358(2)
N1 C4 1.452(2)
N1 C3 1.473(2)
N2 C7 1.375(2)
N2 C6 1.415(2)
N2 C5 1.470(2)
C1 C11 1.520(2)
C1 C2 1.548(2)
C1 C4 1.564(2)
C11 C16 1.379(2)
C11 C12 1.395(3)
C12 C13 1.390(3)
C13 C14 1.375(3)
C14 C15 1.379(3)
C15 C16 1.388(3)
C2 C3 1.539(3)
C4 C5 1.533(2)
C7 C8 1.525(2)
C8 C81 1.521(2)
C81 C86 1.389(3)
C81 C82 1.402(2)
C82 C83 1.387(3)
C83 C84 1.377(4)
C84 C85 1.382(4)
C85 C86 1.390(3)
