#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:33:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178396 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/18/4021808.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_4021808
loop_
_publ_author_name
'Albert Padwa'
'Kenneth R. Crawford'
'Christopher S. Straub'
'Susan N. Pieniazek'
'K. N. Houk'
_publ_section_title
;
 Halo Substituent Effects on Intramolecular Cycloadditions
 Involving Furanyl Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5432
_journal_page_last               5439
_journal_paper_doi               10.1021/jo0602322
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C16 H17 N O2 Cl Br'
_chemical_formula_sum            'C16 H17 Br Cl N O2'
_chemical_formula_weight         370.67
_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                79.169(7)
_cell_angle_beta                 75.112(8)
_cell_angle_gamma                85.849(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5420(8)
_cell_length_b                   11.3679(12)
_cell_length_c                   11.5336(12)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      10.01
_cell_volume                     813.92(16)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_method       'ω scans'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4239
_diffrn_reflns_theta_full        56.74
_diffrn_reflns_theta_max         56.74
_diffrn_reflns_theta_min         3.96
_diffrn_standards_decay_%        3.7
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.981
_exptl_absorpt_correction_T_max  0.1750
_exptl_absorpt_correction_T_min  0.0643
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0024(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   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0350
_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)+(0.0242P)²+0.6280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                2054
_reflns_number_total             2155
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0602322si20060205_013903.cif
_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_database_code               4021808
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
Br Br 0.47338(9) 0.50190(4) 0.32152(4) 0.1006(3) Uani 1 1 d .
Cl1 Cl 0.61924(13) 0.97020(7) 0.18087(8) 0.0642(3) Uani 1 1 d .
O2 O 0.9556(3) 0.7929(2) 0.0818(2) 0.0570(6) Uani 1 1 d .
O1 O 0.8578(3) 1.00972(18) -0.1201(2) 0.0581(6) Uani 1 1 d .
C1 C 0.8707(5) 0.8997(3) -0.0995(3) 0.0525(8) Uani 1 1 d .
N1 N 0.9714(4) 0.8287(2) -0.1790(3) 0.0622(7) Uani 1 1 d .
C7 C 0.7585(5) 0.6992(3) -0.0204(3) 0.0539(8) Uani 1 1 d .
C2 C 0.7885(5) 0.8165(3) 0.0220(3) 0.0489(7) Uani 1 1 d .
C8 C 0.9555(6) 0.7010(3) -0.1269(3) 0.0652(9) Uani 1 1 d .
H8A H 1.0799 0.6708 -0.0985 0.078 Uiso 1 1 calc R
H8B H 0.9363 0.6544 -0.1854 0.078 Uiso 1 1 calc R
C6 C 0.7415(6) 0.5971(3) 0.0874(3) 0.0638(9) Uani 1 1 d .
H6A H 0.7003 0.5246 0.0674 0.077 Uiso 1 1 calc R
H6B H 0.8772 0.5818 0.1076 0.077 Uiso 1 1 calc R
C11 C 0.9849(6) 0.8306(3) -0.3940(3) 0.0653(9) Uani 1 1 d .
C3 C 0.5825(5) 0.8490(3) 0.1083(3) 0.0526(8) Uani 1 1 d .
H3A H 0.4762 0.8738 0.0615 0.063 Uiso 1 1 calc R
C4 C 0.5041(5) 0.7425(3) 0.2039(3) 0.0617(9) Uani 1 1 d .
H4A H 0.3995 0.7542 0.2729 0.074 Uiso 1 1 calc R
C5 C 0.5783(6) 0.6324(3) 0.1938(3) 0.0649(9) Uani 1 1 d .
C10 C 1.0846(6) 0.8713(4) -0.3044(3) 0.0764(11) Uani 1 1 d .
H10A H 1.2301 0.8418 -0.3170 0.092 Uiso 1 1 calc R
H10B H 1.0857 0.9582 -0.3192 0.092 Uiso 1 1 calc R
C9 C 0.5610(6) 0.7053(3) -0.0708(3) 0.0663(9) Uani 1 1 d .
H9A H 0.5485 0.6309 -0.0961 0.100 Uiso 1 1 calc R
H9B H 0.5738 0.7694 -0.1393 0.100 Uiso 1 1 calc R
H9C H 0.4374 0.7193 -0.0085 0.100 Uiso 1 1 calc R
C15 C 0.7028(7) 0.8436(4) -0.4936(4) 0.0914(13) Uani 1 1 d .
H15A H 0.5764 0.8796 -0.5066 0.110 Uiso 1 1 calc R
C16 C 0.7980(7) 0.8822(4) -0.4143(4) 0.0781(11) Uani 1 1 d .
H16A H 0.7346 0.9441 -0.3739 0.094 Uiso 1 1 calc R
C12 C 1.0741(7) 0.7387(4) -0.4543(4) 0.0815(11) Uani 1 1 d .
H12A H 1.2004 0.7022 -0.4417 0.098 Uiso 1 1 calc R
C13 C 0.9764(9) 0.7000(4) -0.5342(4) 0.0977(14) Uani 1 1 d .
H13A H 1.0372 0.6376 -0.5745 0.117 Uiso 1 1 calc R
C14 C 0.7930(9) 0.7532(5) -0.5529(4) 0.0968(14) Uani 1 1 d .
H14A H 0.7286 0.7278 -0.6066 0.116 Uiso 1 1 calc R
H2 H 0.984(5) 0.853(3) 0.093(3) 0.060(11) 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
O1 C1 N1 126.3(3)
O1 C1 C2 127.4(3)
N1 C1 C2 106.2(3)
C1 N1 C10 124.8(3)
C1 N1 C8 113.1(3)
C10 N1 C8 122.1(3)
C6 C7 C8 117.7(3)
C6 C7 C9 110.1(3)
C8 C7 C9 108.5(3)
C6 C7 C2 108.2(3)
C8 C7 C2 99.7(2)
C9 C7 C2 112.2(2)
O2 C2 C3 111.5(3)
O2 C2 C1 108.0(2)
C3 C2 C1 119.5(3)
O2 C2 C7 106.3(2)
C3 C2 C7 108.7(2)
C1 C2 C7 101.7(2)
N1 C8 C7 102.1(3)
C5 C6 C7 108.3(3)
C16 C11 C12 118.3(4)
C16 C11 C10 120.5(3)
C12 C11 C10 121.2(4)
C4 C3 C2 110.1(3)
C4 C3 Cl1 109.2(2)
C2 C3 Cl1 110.9(2)
C5 C4 C3 122.3(3)
C4 C5 C6 125.9(3)
C4 C5 Br 119.7(3)
C6 C5 Br 114.5(2)
N1 C10 C11 111.9(3)
C14 C15 C16 120.2(4)
C11 C16 C15 120.9(4)
C11 C12 C13 120.4(4)
C14 C13 C12 119.9(4)
C13 C14 C15 120.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C5 1.910(3)
Cl1 C3 1.801(3)
O2 C2 1.421(4)
O1 C1 1.229(4)
C1 N1 1.348(4)
C1 C2 1.528(5)
N1 C10 1.454(5)
N1 C8 1.463(4)
C7 C6 1.520(5)
C7 C8 1.533(5)
C7 C9 1.540(4)
C7 C2 1.546(4)
C2 C3 1.523(4)
C6 C5 1.502(5)
C11 C16 1.373(6)
C11 C12 1.375(5)
C11 C10 1.509(5)
C3 C4 1.497(5)
C4 C5 1.325(5)
C15 C14 1.356(6)
C15 C16 1.379(6)
C12 C13 1.396(6)
C13 C14 1.353(7)
