#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:30:12 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151621.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_7151621
loop_
_publ_author_name
'Hermitage, Stephen'
'Howard, Judith A. K.'
'Jay, David'
'Pritchard, Robin G.'
'Probert, Michael R.'
'Whiting, Andrew'
_publ_section_title
;
 Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl
 imines: evidence for the non-concertedness under Lewis-acid catalysed
 conditions.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2451
_journal_page_last               2460
_journal_paper_doi               10.1039/b407293f
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_name_common
;
Ethyl-5-acetyl-8-methoxy-3a,4,5,9b-tetrahydro-3H-
cyclopenta(c)quinoline -4-carboxylate
;
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                67.610(2)
_cell_angle_beta                 83.860(2)
_cell_angle_gamma                66.887(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2885(4)
_cell_length_b                   9.7175(4)
_cell_length_c                   10.1841(5)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.979
_cell_measurement_theta_min      2.367
_cell_volume                     780.73(6)
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_collection       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_reduction        'SMART-NT V5.0 (Bruker, 1998)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART CCD 6K 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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7014
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0490
_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)+(0.0811P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                3097
_reflns_number_total             4517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b407293f.txt
_cod_data_source_block           02srv184
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7151621
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.49036(12) 0.32942(13) 1.18180(11) 0.0277(2) Uani 1 1 d . . .
O2 O 0.84164(13) 0.25104(12) 0.72193(11) 0.0260(2) Uani 1 1 d . . .
O3 O 0.88362(13) 0.18649(12) 0.52777(11) 0.0267(2) Uani 1 1 d . . .
N1 N 0.83279(14) -0.05876(13) 0.87924(12) 0.0204(3) Uani 1 1 d . . .
O4 O 0.99646(14) -0.29090(12) 0.85594(12) 0.0305(3) Uani 1 1 d . . .
C5 C 0.74131(16) 0.03551(16) 0.96011(14) 0.0191(3) Uani 1 1 d . . .
C7 C 0.50021(16) 0.23851(16) 0.98694(15) 0.0204(3) Uani 1 1 d . . .
H7A H 0.3947 0.3089 0.9562 0.025 Uiso 1 1 calc R . .
C6 C 0.58766(16) 0.13960(16) 0.91270(14) 0.0191(3) Uani 1 1 d . . .
C3 C 0.72074(16) 0.13111(17) 1.15057(15) 0.0217(3) Uani 1 1 d . . .
H3A H 0.7661 0.1274 1.2318 0.026 Uiso 1 1 calc R . .
C4 C 0.80797(16) 0.03386(16) 1.07781(15) 0.0203(3) Uani 1 1 d . . .
H4A H 0.9141 -0.0347 1.1079 0.024 Uiso 1 1 calc R . .
C12 C 0.62530(17) 0.05033(17) 0.69778(15) 0.0223(3) Uani 1 1 d . . .
H12A H 0.6129 -0.0551 0.7294 0.027 Uiso 1 1 calc R . .
C2 C 0.56631(16) 0.23470(16) 1.10518(15) 0.0213(3) Uani 1 1 d . . .
C8 C 0.51458(16) 0.15168(16) 0.78077(15) 0.0213(3) Uani 1 1 d . . .
H8A H 0.4249 0.1158 0.8102 0.026 Uiso 1 1 calc R . .
C14 C 0.84167(16) 0.16581(17) 0.66185(14) 0.0209(3) Uani 1 1 d . . .
C13 C 0.79834(17) 0.01844(16) 0.72490(14) 0.0214(3) Uani 1 1 d . . .
H13A H 0.8652 -0.0610 0.6816 0.026 Uiso 1 1 calc R . .
C17 C 0.92295(16) -0.22098(16) 0.93431(15) 0.0216(3) Uani 1 1 d . . .
C18 C 0.92833(17) -0.31237(17) 1.09219(15) 0.0239(3) Uani 1 1 d . . .
H18A H 0.9971 -0.4257 1.1146 0.036 Uiso 0.50 1 calc PR . .
H18B H 0.8225 -0.3048 1.1220 0.036 Uiso 0.50 1 calc PR . .
H18C H 0.9689 -0.2660 1.1427 0.036 Uiso 0.50 1 calc PR . .
H18D H 0.8619 -0.2386 1.1382 0.036 Uiso 0.50 1 calc PR . .
H18E H 1.0365 -0.3596 1.1309 0.036 Uiso 0.50 1 calc PR . .
H18F H 0.8900 -0.3983 1.1102 0.036 Uiso 0.50 1 calc PR . .
C11 C 0.56537(19) 0.14836(18) 0.54054(16) 0.0268(3) Uani 1 1 d . . .
H11A H 0.6535 0.1423 0.4762 0.032 Uiso 1 1 calc R . .
H11B H 0.4938 0.1096 0.5129 0.032 Uiso 1 1 calc R . .
C9 C 0.45277(18) 0.31933(17) 0.66714(16) 0.0260(3) Uani 1 1 d . . .
H9A H 0.4006 0.4149 0.6866 0.031 Uiso 1 1 calc R . .
C15 C 0.9271(2) 0.32499(19) 0.45252(16) 0.0295(3) Uani 1 1 d . . .
H15A H 0.8579 0.4168 0.4792 0.035 Uiso 1 1 calc R . .
H15B H 0.9114 0.3572 0.3488 0.035 Uiso 1 1 calc R . .
C1 C 0.33243(18) 0.43996(18) 1.13710(18) 0.0287(3) Uani 1 1 d . . .
H1A H 0.2922 0.4999 1.2006 0.043 Uiso 1 1 calc R . .
H1B H 0.2672 0.3803 1.1405 0.043 Uiso 1 1 calc R . .
H1C H 0.3297 0.5155 1.0396 0.043 Uiso 1 1 calc R . .
C10 C 0.47994(19) 0.31707(18) 0.53788(16) 0.0286(3) Uani 1 1 d . . .
H10A H 0.4493 0.4107 0.4533 0.034 Uiso 1 1 calc R . .
C16 C 1.0949(2) 0.2873(2) 0.4870(2) 0.0371(4) Uani 1 1 d . . .
H16A H 1.1201 0.3824 0.4349 0.056 Uiso 1 1 calc R . .
H16B H 1.1637 0.1977 0.4591 0.056 Uiso 1 1 calc R . .
H16C H 1.1102 0.2573 0.5894 0.056 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 O1 C1 117.78(11) . . ?
C14 O3 C15 116.12(11) . . ?
C17 N1 C5 125.44(11) . . ?
C17 N1 C13 117.85(11) . . ?
C5 N1 C13 115.30(11) . . ?
C6 C5 C4 120.04(12) . . ?
C6 C5 N1 118.72(12) . . ?
C4 C5 N1 121.03(12) . . ?
C2 C7 C6 120.68(12) . . ?
C2 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C5 C6 C7 119.04(12) . . ?
C5 C6 C8 121.55(12) . . ?
C7 C6 C8 119.39(12) . . ?
C4 C3 C2 120.09(13) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.47(13) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C11 C12 C13 113.79(12) . . ?
C11 C12 C8 104.78(11) . . ?
C13 C12 C8 111.03(11) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C8 C12 H12A 109.0 . . ?
O1 C2 C7 124.42(12) . . ?
O1 C2 C3 115.92(12) . . ?
C7 C2 C3 119.65(13) . . ?
C6 C8 C9 114.64(11) . . ?
C6 C8 C12 115.58(11) . . ?
C9 C8 C12 102.39(11) . . ?
C6 C8 H8A 107.9 . . ?
C9 C8 H8A 107.9 . . ?
C12 C8 H8A 107.9 . . ?
O2 C14 O3 123.99(13) . . ?
O2 C14 C13 126.16(13) . . ?
O3 C14 C13 109.83(11) . . ?
N1 C13 C14 111.14(11) . . ?
N1 C13 C12 107.52(11) . . ?
C14 C13 C12 115.32(11) . . ?
N1 C13 H13A 107.5 . . ?
C14 C13 H13A 107.5 . . ?
C12 C13 H13A 107.5 . . ?
O4 C17 N1 120.46(13) . . ?
O4 C17 C18 120.29(12) . . ?
N1 C17 C18 119.24(12) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C17 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C10 C11 C12 102.88(12) . . ?
C10 C11 H11A 111.2 . . ?
C12 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C12 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C10 C9 C8 112.06(13) . . ?
C10 C9 H9A 124.0 . . ?
C8 C9 H9A 124.0 . . ?
O3 C15 C16 111.56(13) . . ?
O3 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O3 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 C11 111.92(13) . . ?
C9 C10 H10A 124.0 . . ?
C11 C10 H10A 124.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 C2 1.3687(16) . ?
O1 C1 1.4304(18) . ?
O2 C14 1.2026(17) . ?
O3 C14 1.3398(17) . ?
O3 C15 1.4618(18) . ?
N1 C17 1.3753(17) . ?
N1 C5 1.4330(17) . ?
N1 C13 1.4685(18) . ?
O4 C17 1.2235(17) . ?
C5 C6 1.3911(19) . ?
C5 C4 1.3988(19) . ?
C7 C2 1.391(2) . ?
C7 C6 1.4016(19) . ?
C7 H7A 0.9500 . ?
C6 C8 1.5140(19) . ?
C3 C4 1.3793(18) . ?
C3 C2 1.3922(19) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9500 . ?
C12 C11 1.547(2) . ?
C12 C13 1.547(2) . ?
C12 C8 1.5475(19) . ?
C12 H12A 1.0000 . ?
C8 C9 1.5147(19) . ?
C8 H8A 1.0000 . ?
C14 C13 1.524(2) . ?
C13 H13A 1.0000 . ?
C17 C18 1.507(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C11 C10 1.506(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C9 C10 1.320(2) . ?
C9 H9A 0.9500 . ?
C15 C16 1.502(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 H10A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
