#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:47:27 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178916 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/45/4114505.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_4114505
loop_
_publ_author_name
'Jik Chin'
'Fabrizio Mancin'
'Nirusha Thavarajah'
'Donghyung Lee'
'Alan Lough'
'Doo Soo Chung'
_publ_section_title
;
 Controlling Diaza-Cope Rearrangement Reactions with Resonance-Assisted
 Hydrogen Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15276
_journal_page_last               15277
_journal_paper_doi               10.1021/ja0387554
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C30 H28 N2 O4, C H Cl3, C H4 O'
_chemical_formula_sum            'C32 H33 Cl3 N2 O5'
_chemical_formula_weight         631.95
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.690(2)
_cell_angle_beta                 101.930(2)
_cell_angle_gamma                95.511(2)
_cell_formula_units_Z            1
_cell_length_a                   6.7660(3)
_cell_length_b                   10.2215(4)
_cell_length_c                   11.6018(6)
_cell_measurement_reflns_used    13687
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.6
_cell_volume                     732.15(6)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.12'
_computing_publication_material  'SHELXTL V6.12'
_computing_structure_refinement  'SHELXTL V6.12(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0954
_diffrn_reflns_av_sigmaI/netI    0.0999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9007
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       plate
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.13(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0852
_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)+(0.1325P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2328
_reflns_number_gt                1681
_reflns_number_total             2557
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja0387554si20030929_024325.cif
_cod_data_source_block           k02164
_cod_database_code               4114505
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
O1 O 0.4389(3) 0.4733(2) 0.6254(2) 0.0375(7) Uani 1 1 d .
O2 O -0.1609(4) -0.0457(2) 0.2116(2) 0.0457(7) Uani 1 1 d .
N1 N 0.1115(4) 0.3402(2) 0.4404(2) 0.0280(6) Uani 1 1 d .
C1 C -0.0026(5) 0.4309(3) 0.5170(3) 0.0261(7) Uani 1 1 d .
H1 H -0.1479 0.3827 0.4964 0.031 Uiso 1 1 calc R
C2 C 0.0946(5) 0.4680(3) 0.6557(3) 0.0267(7) Uani 1 1 d .
C3 C 0.3076(5) 0.4922(3) 0.7031(3) 0.0295(7) Uani 1 1 d .
C4 C 0.3923(5) 0.5414(3) 0.8321(3) 0.0364(8) Uani 1 1 d .
H4A H 0.5370 0.5578 0.8639 0.044 Uiso 1 1 calc R
C5 C 0.2680(5) 0.5665(3) 0.9143(3) 0.0370(8) Uani 1 1 d .
H5A H 0.3272 0.6015 1.0025 0.044 Uiso 1 1 calc R
C6 C 0.0569(5) 0.5405(3) 0.8683(3) 0.0336(8) Uani 1 1 d .
H6A H -0.0294 0.5563 0.9247 0.040 Uiso 1 1 calc R
C7 C -0.0276(5) 0.4915(3) 0.7401(3) 0.0307(8) Uani 1 1 d .
H7A H -0.1725 0.4734 0.7090 0.037 Uiso 1 1 calc R
C8 C 0.0117(5) 0.2281(3) 0.3524(3) 0.0275(7) Uani 1 1 d .
H8A H -0.1308 0.2015 0.3430 0.033 Uiso 1 1 calc R
C9 C 0.1162(5) 0.1397(3) 0.2651(3) 0.0309(8) Uani 1 1 d .
C10 C 0.3041(5) 0.1912(3) 0.2508(3) 0.0366(8) Uani 1 1 d .
H10A H 0.3681 0.2855 0.2987 0.044 Uiso 1 1 calc R
C11 C 0.3982(6) 0.1076(4) 0.1684(3) 0.0430(9) Uani 1 1 d .
H11A H 0.5264 0.1441 0.1595 0.052 Uiso 1 1 calc R
C12 C 0.3061(6) -0.0300(4) 0.0983(3) 0.0475(10) Uani 1 1 d .
H12A H 0.3717 -0.0874 0.0412 0.057 Uiso 1 1 calc R
C13 C 0.1204(6) -0.0846(4) 0.1105(3) 0.0446(9) Uani 1 1 d .
H13A H 0.0600 -0.1796 0.0626 0.053 Uiso 1 1 calc R
C14 C 0.0211(5) -0.0019(3) 0.1922(3) 0.0342(8) Uani 1 1 d .
C15 C -0.2446(7) -0.1914(4) 0.1574(4) 0.0559(11) Uani 1 1 d .
H15A H -0.3765 -0.2082 0.1772 0.084 Uiso 1 1 calc R
H15B H -0.1497 -0.2443 0.1916 0.084 Uiso 1 1 calc R
H15C H -0.2650 -0.2222 0.0659 0.084 Uiso 1 1 calc R
H1O H 0.349(7) 0.416(5) 0.544(5) 0.062(13) 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 0.0033 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_3
C14 O2 C15 117.9(3) .
C8 N1 C1 118.2(3) .
N1 C1 C2 111.0(2) .
N1 C1 C1 107.0(3) 2_566
C2 C1 C1 109.6(3) 2_566
C7 C2 C3 118.4(3) .
C7 C2 C1 119.6(3) .
C3 C2 C1 121.7(3) .
O1 C3 C4 118.1(3) .
O1 C3 C2 121.8(3) .
C4 C3 C2 120.1(3) .
C5 C4 C3 120.5(3) .
C4 C5 C6 119.9(3) .
C7 C6 C5 119.6(3) .
C6 C7 C2 121.5(3) .
N1 C8 C9 120.4(3) .
C10 C9 C14 119.1(3) .
C10 C9 C8 121.7(3) .
C14 C9 C8 119.2(3) .
C11 C10 C9 120.9(3) .
C10 C11 C12 120.0(4) .
C13 C12 C11 120.7(3) .
C12 C13 C14 120.5(3) .
O2 C14 C13 125.1(3) .
O2 C14 C9 116.0(3) .
C13 C14 C9 118.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.376(4) .
O2 C14 1.357(4) .
O2 C15 1.424(4) .
N1 C8 1.276(4) .
N1 C1 1.463(4) .
C1 C2 1.512(4) .
C1 C1 1.583(6) 2_566
C2 C7 1.386(4) .
C2 C3 1.399(4) .
C3 C4 1.389(5) .
C4 C5 1.378(5) .
C5 C6 1.385(5) .
C6 C7 1.381(5) .
C8 C9 1.475(4) .
C9 C10 1.391(5) .
C9 C14 1.427(4) .
C10 C11 1.371(5) .
C11 C12 1.384(5) .
C12 C13 1.379(6) .
C13 C14 1.386(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O N1 0.97(5) 1.73(5) 2.636(3) 154(4)
