#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/28/4022845.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_4022845
loop_
_publ_author_name
'Cyril Poriel'
'Mathilde Lachia'
'Claire Wilson'
'James R. Davies'
'Christopher J. Moody'
_publ_contact_author             'Prof. C.J. Moody'
_publ_contact_author_address
;
School of Chemistry
University of Nottingham
University Park
Nottingham
NG7 2RD
;
_publ_contact_author_email       c.j.moody@nottingham.ac.uk
_publ_section_title
;
 Oxidative Rearrangement of Indoles: A New Approach to
 the EFHG-Tetracyclic Core of Diazonamide A
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2978
_journal_page_last               2987
_journal_paper_doi               10.1021/jo062627r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C17 H15 Br N2 O3'
_chemical_formula_weight         375.22
_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                86.396(1)
_cell_angle_beta                 77.900(1)
_cell_angle_gamma                71.556(1)
_cell_formula_units_Z            2
_cell_length_a                   7.9118(7)
_cell_length_b                   9.4898(8)
_cell_length_c                   11.6979(10)
_cell_measurement_reflns_used    2892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.75
_cell_volume                     814.66(12)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6878
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS v2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0444P)²+0.4647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                3179
_reflns_number_total             3625
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo062627rsi20070130_025609_1.cif
_cod_data_source_block           4c
_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               4022845
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
Br1 Br 0.18477(3) 0.03415(3) 0.90271(2) 0.03534(10) Uani 1 1 d .
O1 O 0.1094(2) 0.62657(17) 0.92165(13) 0.0252(3) Uani 1 1 d .
N1 N 0.1576(2) 0.38380(19) 0.87474(15) 0.0199(4) Uani 1 1 d .
H1A H 0.0829 0.3614 0.9348 0.024 Uiso 1 1 calc R
O2 O 0.4763(2) 0.68708(17) 0.67134(13) 0.0255(3) Uani 1 1 d .
N2 N 0.5733(3) 0.5144(2) 0.80138(16) 0.0254(4) Uani 1 1 d .
C2 C 0.1785(3) 0.5207(2) 0.85526(17) 0.0187(4) Uani 1 1 d .
O3 O 0.5220(2) 0.41395(18) 0.88370(13) 0.0279(3) Uani 1 1 d .
C3A C 0.3598(3) 0.3567(2) 0.70038(17) 0.0163(4) Uani 1 1 d .
C3 C 0.2963(3) 0.5207(2) 0.73130(17) 0.0165(4) Uani 1 1 d .
C4 C 0.4845(3) 0.2780(2) 0.60680(18) 0.0200(4) Uani 1 1 d .
H4A H 0.5471 0.3270 0.5476 0.024 Uiso 1 1 calc R
C5 C 0.5163(3) 0.1255(2) 0.60124(19) 0.0240(4) Uani 1 1 d .
H5A H 0.6006 0.0706 0.5368 0.029 Uiso 1 1 calc R
C6 C 0.4281(3) 0.0517(2) 0.6874(2) 0.0254(5) Uani 1 1 d .
H6A H 0.4527 -0.0526 0.6825 0.030 Uiso 1 1 calc R
C7 C 0.3033(3) 0.1318(2) 0.78102(18) 0.0225(4) Uani 1 1 d .
C7A C 0.2699(3) 0.2831(2) 0.78720(17) 0.0179(4) Uani 1 1 d .
C8 C 0.1748(3) 0.6195(2) 0.65153(18) 0.0193(4) Uani 1 1 d .
C9 C 0.1687(3) 0.5691(2) 0.54409(19) 0.0239(4) Uani 1 1 d .
H9A H 0.2372 0.4704 0.5194 0.029 Uiso 1 1 calc R
C10 C 0.0619(3) 0.6637(3) 0.4724(2) 0.0305(5) Uani 1 1 d .
H10A H 0.0595 0.6291 0.3985 0.037 Uiso 1 1 calc R
C11 C -0.0401(3) 0.8065(3) 0.5073(2) 0.0371(6) Uani 1 1 d .
H11A H -0.1132 0.8700 0.4582 0.045 Uiso 1 1 calc R
C12 C -0.0351(4) 0.8565(3) 0.6147(2) 0.0379(6) Uani 1 1 d .
H12A H -0.1060 0.9547 0.6397 0.046 Uiso 1 1 calc R
C13 C 0.0726(3) 0.7648(2) 0.6864(2) 0.0292(5) Uani 1 1 d .
H13A H 0.0767 0.8009 0.7594 0.035 Uiso 1 1 calc R
C14 C 0.4547(3) 0.5833(2) 0.73259(17) 0.0182(4) Uani 1 1 d .
C15 C 0.6997(3) 0.5836(3) 0.8301(2) 0.0356(6) Uani 1 1 d .
H15A H 0.7255 0.6521 0.7675 0.053 Uiso 1 1 calc R
H15B H 0.8132 0.5067 0.8383 0.053 Uiso 1 1 calc R
H15C H 0.6455 0.6387 0.9038 0.053 Uiso 1 1 calc R
C16 C 0.6610(4) 0.2712(3) 0.8693(3) 0.0421(6) Uani 1 1 d .
H16A H 0.6245 0.2018 0.9274 0.063 Uiso 1 1 calc R
H16B H 0.7758 0.2819 0.8803 0.063 Uiso 1 1 calc R
H16C H 0.6770 0.2330 0.7906 0.063 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'
Br Br -0.2901 2.4595 '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
C2 N1 C7A 111.41(16)
C14 N2 O3 116.80(16)
C14 N2 C15 121.26(19)
O3 N2 C15 116.14(17)
O1 C2 N1 125.72(18)
O1 C2 C3 126.14(18)
N1 C2 C3 108.05(16)
N2 O3 C16 109.94(18)
C4 C3A C7A 120.09(18)
C4 C3A C3 131.21(18)
C7A C3A C3 108.70(16)
C3A C3 C8 113.66(16)
C3A C3 C2 101.11(15)
C8 C3 C2 108.53(15)
C3A C3 C14 113.31(16)
C8 C3 C14 108.37(15)
C2 C3 C14 111.68(16)
C3A C4 C5 118.57(19)
C6 C5 C4 121.57(19)
C5 C6 C7 119.4(2)
C7A C7 C6 119.61(19)
C7A C7 Br1 119.77(16)
C6 C7 Br1 120.58(16)
C7 C7A C3A 120.79(18)
C7 C7A N1 129.42(18)
C3A C7A N1 109.73(17)
C9 C8 C13 119.2(2)
C9 C8 C3 121.59(18)
C13 C8 C3 119.22(19)
C8 C9 C10 119.9(2)
C11 C10 C9 120.9(2)
C10 C11 C12 119.3(2)
C11 C12 C13 120.7(2)
C12 C13 C8 120.1(2)
O2 C14 N2 120.66(18)
O2 C14 C3 121.97(18)
N2 C14 C3 117.32(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C7 1.895(2)
O1 C2 1.218(2)
N1 C2 1.360(3)
N1 C7A 1.398(3)
O2 C14 1.216(2)
N2 C14 1.348(3)
N2 O3 1.402(2)
N2 C15 1.460(3)
C2 C3 1.550(3)
O3 C16 1.442(3)
C3A C4 1.383(3)
C3A C7A 1.396(3)
C3A C3 1.518(3)
C3 C8 1.539(3)
C3 C14 1.551(3)
C4 C5 1.392(3)
C5 C6 1.385(3)
C6 C7 1.389(3)
C7 C7A 1.378(3)
C8 C9 1.388(3)
C8 C13 1.396(3)
C9 C10 1.395(3)
C10 C11 1.376(4)
C11 C12 1.383(4)
C12 C13 1.387(3)
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
_geom_hbond_site_symmetry_A
N1 H1A O1 0.88 2.00 2.853(2) 163.6 2_567
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7A N1 C2 O1 -173.8(2)
C7A N1 C2 C3 9.4(2)
C14 N2 O3 C16 125.4(2)
C15 N2 O3 C16 -81.1(2)
C4 C3A C3 C8 71.6(3)
C7A C3A C3 C8 -108.98(18)
C4 C3A C3 C2 -172.3(2)
C7A C3A C3 C2 7.1(2)
C4 C3A C3 C14 -52.7(3)
C7A C3A C3 C14 126.73(17)
O1 C2 C3 C3A 173.3(2)
N1 C2 C3 C3A -9.9(2)
O1 C2 C3 C8 -66.9(3)
N1 C2 C3 C8 109.93(18)
O1 C2 C3 C14 52.5(3)
N1 C2 C3 C14 -130.67(17)
C7A C3A C4 C5 0.5(3)
C3 C3A C4 C5 179.8(2)
C3A C4 C5 C6 -0.8(3)
C4 C5 C6 C7 0.7(3)
C5 C6 C7 C7A -0.4(3)
C5 C6 C7 Br1 -178.29(16)
C6 C7 C7A C3A 0.1(3)
Br1 C7 C7A C3A 178.03(15)
C6 C7 C7A N1 -176.8(2)
Br1 C7 C7A N1 1.1(3)
C4 C3A C7A C7 -0.2(3)
C3 C3A C7A C7 -179.64(19)
C4 C3A C7A N1 177.33(18)
C3 C3A C7A N1 -2.1(2)
C2 N1 C7A C7 172.5(2)
C2 N1 C7A C3A -4.8(2)
C3A C3 C8 C9 -17.3(3)
C2 C3 C8 C9 -128.9(2)
C14 C3 C8 C9 109.6(2)
C3A C3 C8 C13 164.73(18)
C2 C3 C8 C13 53.1(2)
C14 C3 C8 C13 -68.4(2)
C13 C8 C9 C10 0.2(3)
C3 C8 C9 C10 -177.73(19)
C8 C9 C10 C11 -0.8(3)
C9 C10 C11 C12 0.4(4)
C10 C11 C12 C13 0.5(4)
C11 C12 C13 C8 -1.1(4)
C9 C8 C13 C12 0.7(3)
C3 C8 C13 C12 178.8(2)
O3 N2 C14 O2 169.19(18)
C15 N2 C14 O2 17.1(3)
O3 N2 C14 C3 -13.3(3)
C15 N2 C14 C3 -165.44(19)
C3A C3 C14 O2 122.3(2)
C8 C3 C14 O2 -4.8(3)
C2 C3 C14 O2 -124.3(2)
C3A C3 C14 N2 -55.2(2)
C8 C3 C14 N2 177.73(17)
C2 C3 C14 N2 58.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17284455
