#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/34/1503436.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_1503436
loop_
_publ_author_name
'Xiao, Jian'
'Xu, Feng-Xia'
'Lu, Yun-Peng'
'Loh, Teck-Peng'
_publ_section_title
;
 Chemzymes: a new class of structurally rigid tricyclic amphibian
 organocatalyst inspired by natural product.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1220
_journal_page_last               1223
_journal_paper_doi               10.1021/ol9029758
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H18 N2 O4'
_chemical_formula_sum            'C15 H18 N2 O4'
_chemical_formula_weight         290.31
_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                   7.9402(2)
_cell_length_b                   11.7992(3)
_cell_length_c                   15.7954(4)
_cell_measurement_reflns_used    8324
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      2.58
_cell_volume                     1479.84(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35185
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041
_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   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0634P)²+0.2885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                1922
_reflns_number_total             2575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9029758_si_001.cif
_cod_data_source_block           ltp58
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503436
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
_atom_site_refinement_flags
C1 C 1.0485(7) 0.0167(3) 0.5180(3) 0.1000(15) Uani 1 1 d .
H1A H 0.9403 -0.0198 0.5174 0.150 Uiso 1 1 calc R
H1B H 1.1123 -0.0100 0.5656 0.150 Uiso 1 1 calc R
H1C H 1.1076 -0.0008 0.4666 0.150 Uiso 1 1 calc R
C2 C 0.9377(3) 0.1729(2) 0.59181(15) 0.0479(5) Uani 1 1 d .
C3 C 0.9118(3) 0.3018(2) 0.58848(15) 0.0497(6) Uani 1 1 d .
H3 H 0.8386 0.3196 0.5403 0.060 Uiso 1 1 calc R
C4 C 1.0732(4) 0.3711(2) 0.58038(15) 0.0544(6) Uani 1 1 d .
H4A H 1.0511 0.4444 0.5550 0.065 Uiso 1 1 calc R
H4B H 1.1565 0.3314 0.5466 0.065 Uiso 1 1 calc R
C5 C 1.1322(4) 0.3838(2) 0.67252(15) 0.0506(6) Uani 1 1 d .
H5 H 1.1886 0.4567 0.6818 0.061 Uiso 1 1 calc R
C6 C 0.9685(3) 0.3742(2) 0.72571(14) 0.0472(5) Uani 1 1 d .
H6 H 0.9449 0.4454 0.7554 0.057 Uiso 1 1 calc R
C7 C 1.1607(3) 0.2285(2) 0.76812(14) 0.0468(5) Uani 1 1 d .
C8 C 1.2316(4) 0.1328(2) 0.80458(18) 0.0567(6) Uani 1 1 d .
H8 H 1.1780 0.0944 0.8484 0.068 Uiso 1 1 calc R
C9 C 1.3856(4) 0.0967(3) 0.7731(2) 0.0680(8) Uani 1 1 d .
H9 H 1.4362 0.0328 0.7963 0.082 Uiso 1 1 calc R
C10 C 1.4651(4) 0.1534(3) 0.7082(2) 0.0673(8) Uani 1 1 d .
H10 H 1.5683 0.1274 0.6884 0.081 Uiso 1 1 calc R
C11 C 1.3933(4) 0.2486(3) 0.67232(19) 0.0601(7) Uani 1 1 d .
H11 H 1.4475 0.2867 0.6286 0.072 Uiso 1 1 calc R
C12 C 1.2391(3) 0.2862(2) 0.70253(16) 0.0492(5) Uani 1 1 d .
C13 C 0.8946(4) 0.2469(2) 0.84769(15) 0.0540(6) Uani 1 1 d .
C14 C 0.6318(4) 0.2907(3) 0.91158(18) 0.0684(8) Uani 1 1 d .
H14A H 0.6811 0.2985 0.9674 0.082 Uiso 1 1 calc R
H14B H 0.5891 0.2141 0.9056 0.082 Uiso 1 1 calc R
C15 C 0.4938(4) 0.3738(3) 0.9002(2) 0.0761(9) Uani 1 1 d .
H15A H 0.4483 0.3667 0.8441 0.114 Uiso 1 1 calc R
H15B H 0.5368 0.4491 0.9080 0.114 Uiso 1 1 calc R
H15C H 0.4068 0.3594 0.9410 0.114 Uiso 1 1 calc R
N1 N 0.8375(3) 0.34905(19) 0.66451(13) 0.0506(5) Uani 1 1 d .
H1N H 0.761(4) 0.306(3) 0.687(2) 0.057(9) Uiso 1 1 d .
N2 N 1.0050(3) 0.28145(17) 0.78702(12) 0.0483(5) Uani 1 1 d .
O1 O 1.0261(3) 0.13734(17) 0.52459(12) 0.0680(6) Uani 1 1 d .
O2 O 0.8808(3) 0.11139(17) 0.64396(14) 0.0693(6) Uani 1 1 d .
O3 O 0.9162(3) 0.1685(2) 0.89580(13) 0.0788(7) Uani 1 1 d .
O4 O 0.7566(3) 0.31404(17) 0.84690(11) 0.0603(5) Uani 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 0.0033 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
O2 C2 O1 123.9(2)
O2 C2 C3 125.3(2)
O1 C2 C3 110.7(2)
N1 C3 C4 101.9(2)
N1 C3 C2 114.0(2)
C4 C3 C2 114.9(2)
C3 C4 C5 103.23(19)
C12 C5 C4 113.3(2)
C12 C5 C6 104.22(19)
C4 C5 C6 104.5(2)
N1 C6 N2 115.0(2)
N1 C6 C5 104.77(19)
N2 C6 C5 104.07(19)
C8 C7 C12 121.8(3)
C8 C7 N2 128.7(2)
C12 C7 N2 109.4(2)
C7 C8 C9 117.3(3)
C10 C9 C8 121.5(3)
C9 C10 C11 120.8(3)
C10 C11 C12 118.9(3)
C11 C12 C7 119.7(3)
C11 C12 C5 129.3(2)
C7 C12 C5 110.9(2)
O3 C13 O4 124.6(3)
O3 C13 N2 125.5(3)
O4 C13 N2 109.9(2)
O4 C14 C15 107.1(2)
C3 N1 C6 109.8(2)
C13 N2 C7 125.3(2)
C13 N2 C6 123.6(2)
C7 N2 C6 110.88(19)
C2 O1 C1 115.6(3)
C13 O4 C14 115.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.439(4)
C2 O2 1.187(3)
C2 O1 1.340(3)
C2 C3 1.536(4)
C3 N1 1.450(3)
C3 C4 1.526(4)
C4 C5 1.536(3)
C5 C12 1.507(4)
C5 C6 1.552(4)
C6 N1 1.451(3)
C6 N2 1.490(3)
C7 C8 1.387(4)
C7 C12 1.387(3)
C7 N2 1.417(4)
C8 C9 1.387(5)
C9 C10 1.377(5)
C10 C11 1.381(4)
C11 C12 1.387(4)
C13 O3 1.209(3)
C13 O4 1.353(4)
C13 N2 1.361(3)
C14 O4 1.450(3)
C14 C15 1.481(5)
