#------------------------------------------------------------------------------
#$Date: 2016-01-30 09:21:19 +0200 (Sat, 30 Jan 2016) $
#$Revision: 175315 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/40/7224062.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_7224062
loop_
_publ_author_name
'Du, Ding'
'Lu, Tao'
'Xu, Junyu'
'Zhang, Weiguo'
'Liu, Yishan'
'Liu, Ming'
'Zhu, Suzhen'
'Hua, Xi'
'Chen, Siyi'
_publ_section_title
;
 Formal [3+3] Annulation of Isatin-derived 2-Bromoenals with 1,
 3-Dicarbonyl Compounds Enabled by Lewis Acid/N-Heterocyclic Carbene
 Cooperative Catalysis
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA27848A
_journal_year                    2016
_chemical_formula_sum            'C17 H11 Br2 N O2'
_chemical_formula_weight         421.09
_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
_audit_update_record
;
2015-11-11 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                93.78(3)
_cell_angle_beta                 98.83(3)
_cell_angle_gamma                107.13(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7580(18)
_cell_length_b                   9.0190(18)
_cell_length_c                   10.089(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     747.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0616
_diffrn_reflns_av_sigmaI/netI    0.1283
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2927
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.429
_exptl_absorpt_correction_T_max  0.6128
_exptl_absorpt_correction_T_min  0.4098
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1576
_refine_ls_R_factor_gt           0.0772
_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)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                1445
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra27848a2.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7224062
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
N N 0.4079(9) 0.1576(9) 0.3291(7) 0.0348(19) Uani 1 1 d .
Br1 Br 0.97404(13) 0.74526(12) 0.38823(10) 0.0486(4) Uani 1 1 d .
O1 O 0.4698(9) 0.1762(9) 0.8844(6) 0.061(2) Uani 1 1 d .
C1 C 0.5328(10) 0.2992(9) 0.3260(8) 0.024 Uani 1 1 d .
Br2 Br 0.71933(15) 0.42815(15) 0.79312(12) 0.0680(5) Uani 1 1 d .
O2 O 0.3062(7) 0.0128(8) 0.4909(6) 0.0461(18) Uani 1 1 d .
C2 C 0.5752(10) 0.3645(11) 0.2160(8) 0.034(2) Uani 1 1 d .
H2A H 0.5196 0.3191 0.1299 0.040 Uiso 1 1 calc R
C3 C 0.7070(11) 0.5042(11) 0.2349(9) 0.041(3) Uani 1 1 d .
H3A H 0.7363 0.5547 0.1609 0.049 Uiso 1 1 calc R
C4 C 0.7900(11) 0.5641(10) 0.3606(10) 0.034(2) Uani 1 1 d .
C5 C 0.7441(10) 0.4934(11) 0.4728(8) 0.034(2) Uani 1 1 d .
H5A H 0.8023 0.5361 0.5587 0.041 Uiso 1 1 calc R
C6 C 0.6128(9) 0.3606(10) 0.4568(8) 0.026(2) Uani 1 1 d .
C7 C 0.5340(9) 0.2599(10) 0.5512(8) 0.029(2) Uani 1 1 d .
C8 C 0.4007(11) 0.1239(11) 0.4576(9) 0.038(2) Uani 1 1 d .
C9 C 0.5557(10) 0.2718(10) 0.6859(8) 0.029(2) Uani 1 1 d .
C10 C 0.4445(12) 0.1658(12) 0.7654(11) 0.044(3) Uani 1 1 d .
H10A H 0.3524 0.0893 0.7182 0.053 Uiso 1 1 calc R
C11 C 0.2877(11) 0.0645(11) 0.2096(8) 0.038(3) Uani 1 1 d .
H11A H 0.3426 0.0592 0.1338 0.046 Uiso 1 1 calc R
H11B H 0.2410 -0.0412 0.2301 0.046 Uiso 1 1 calc R
C12 C 0.1559(10) 0.1343(10) 0.1718(9) 0.034(2) Uani 1 1 d .
C13 C 0.0515(11) 0.1443(11) 0.2502(9) 0.038(2) Uani 1 1 d .
H13A H 0.0648 0.1107 0.3351 0.046 Uiso 1 1 calc R
C14 C -0.0754(11) 0.2013(12) 0.2140(9) 0.041(3) Uani 1 1 d .
H14A H -0.1480 0.2037 0.2719 0.050 Uiso 1 1 calc R
C15 C -0.0933(12) 0.2564(12) 0.0867(10) 0.042(3) Uani 1 1 d .
H15A H -0.1749 0.3008 0.0607 0.050 Uiso 1 1 calc R
C16 C 0.0092(12) 0.2438(11) 0.0037(9) 0.038(2) Uani 1 1 d .
H16A H -0.0046 0.2760 -0.0818 0.046 Uiso 1 1 calc R
C17 C 0.1303(12) 0.1860(11) 0.0418(9) 0.039(2) Uani 1 1 d .
H17A H 0.1999 0.1791 -0.0177 0.047 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
C8 N C1 111.4(7)
C8 N C11 123.1(7)
C1 N C11 125.2(7)
C2 C1 C6 123.4(8)
C2 C1 N 126.9(7)
C6 C1 N 109.6(7)
C1 C2 C3 118.0(8)
C1 C2 H2A 121.0
C3 C2 H2A 121.0
C4 C3 C2 119.8(9)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 120.9(8)
C3 C4 Br1 120.8(7)
C5 C4 Br1 118.3(7)
C6 C5 C4 120.1(7)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C5 C6 C1 117.6(8)
C5 C6 C7 133.7(7)
C1 C6 C7 108.6(7)
C9 C7 C6 132.7(8)
C9 C7 C8 123.4(8)
C6 C7 C8 103.9(7)
O2 C8 N 126.0(8)
O2 C8 C7 127.6(8)
N C8 C7 106.4(7)
C7 C9 C10 124.5(8)
C7 C9 Br2 122.3(6)
C10 C9 Br2 113.1(6)
O1 C10 C9 122.9(9)
O1 C10 H10A 118.6
C9 C10 H10A 118.6
C12 C11 N 111.5(8)
C12 C11 H11A 109.3
N C11 H11A 109.3
C12 C11 H11B 109.3
N C11 H11B 109.3
H11A C11 H11B 108.0
C13 C12 C17 116.3(9)
C13 C12 C11 123.1(9)
C17 C12 C11 120.5(9)
C12 C13 C14 123.8(9)
C12 C13 H13A 118.1
C14 C13 H13A 118.1
C13 C14 C15 118.2(8)
C13 C14 H14A 120.9
C15 C14 H14A 120.9
C16 C15 C14 119.0(9)
C16 C15 H15A 120.5
C14 C15 H15A 120.5
C17 C16 C15 121.1(9)
C17 C16 H16A 119.5
C15 C16 H16A 119.5
C16 C17 C12 121.6(9)
C16 C17 H17A 119.2
C12 C17 H17A 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C8 1.358(11)
N C1 1.422(10)
N C11 1.491(10)
Br1 C4 1.896(8)
O1 C10 1.180(11)
C1 C2 1.341(11)
C1 C6 1.390(11)
Br2 C9 1.828(9)
O2 C8 1.202(10)
C2 C3 1.414(12)
C2 H2A 0.9300
C3 C4 1.351(12)
C3 H3A 0.9300
C4 C5 1.391(11)
C5 C6 1.374(11)
C5 H5A 0.9300
C6 C7 1.467(11)
C7 C9 1.336(11)
C7 C8 1.557(11)
C9 C10 1.516(13)
C10 H10A 0.9300
C11 C12 1.483(12)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.316(12)
C12 C17 1.428(12)
C13 C14 1.367(12)
C13 H13A 0.9300
C14 C15 1.411(13)
C14 H14A 0.9300
C15 C16 1.341(13)
C15 H15A 0.9300
C16 C17 1.331(13)
C16 H16A 0.9300
C17 H17A 0.9300
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
C8 N C1 C2 178.4(9)
C11 N C1 C2 -7.5(15)
C8 N C1 C6 0.8(11)
C11 N C1 C6 175.0(8)
C6 C1 C2 C3 -0.9(14)
N C1 C2 C3 -178.1(9)
C1 C2 C3 C4 2.8(14)
C2 C3 C4 C5 -2.4(15)
C2 C3 C4 Br1 176.7(7)
C3 C4 C5 C6 0.1(14)
Br1 C4 C5 C6 -179.0(7)
C4 C5 C6 C1 1.7(13)
C4 C5 C6 C7 -179.8(9)
C2 C1 C6 C5 -1.3(14)
N C1 C6 C5 176.3(8)
C2 C1 C6 C7 179.9(9)
N C1 C6 C7 -2.5(10)
C5 C6 C7 C9 6.8(18)
C1 C6 C7 C9 -174.7(10)
C5 C6 C7 C8 -175.6(10)
C1 C6 C7 C8 3.0(9)
C1 N C8 O2 179.1(10)
C11 N C8 O2 4.9(16)
C1 N C8 C7 1.1(10)
C11 N C8 C7 -173.2(8)
C9 C7 C8 O2 -2.5(16)
C6 C7 C8 O2 179.5(10)
C9 C7 C8 N 175.5(9)
C6 C7 C8 N -2.5(10)
C6 C7 C9 C10 170.7(9)
C8 C7 C9 C10 -6.6(15)
C6 C7 C9 Br2 -5.6(15)
C8 C7 C9 Br2 177.1(7)
C7 C9 C10 O1 177.5(10)
Br2 C9 C10 O1 -5.9(13)
C8 N C11 C12 95.1(11)
C1 N C11 C12 -78.4(11)
N C11 C12 C13 -64.9(11)
N C11 C12 C17 119.1(8)
C17 C12 C13 C14 -0.5(14)
C11 C12 C13 C14 -176.7(8)
C12 C13 C14 C15 -1.7(15)
C13 C14 C15 C16 3.3(14)
C14 C15 C16 C17 -2.6(15)
C15 C16 C17 C12 0.3(14)
C13 C12 C17 C16 1.3(13)
C11 C12 C17 C16 177.5(8)
