#------------------------------------------------------------------------------
#$Date: 2019-11-24 00:36:14 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/72/4037201.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_4037201
loop_
_publ_author_name
'Yang, Yang'
'Ma, Chaoqun'
'Thumar, Nilesh J.'
'Hu, Wenhao'
_publ_section_title
;
 Pd(II)/β-ICD-Cocatalyzed Asymmetric Route to Oxindole Scaffold via
 Cascade Reaction of Diazoacetamides and MBH-Carbonates.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8537
_journal_page_last               8543
_journal_paper_doi               10.1021/acs.joc.6b01703
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C21 H20 Br N O3'
_chemical_formula_weight         414.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                68.3610(10)
_cell_angle_beta                 78.5310(10)
_cell_angle_gamma                83.6200(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4241(3)
_cell_length_b                   10.3964(3)
_cell_length_c                   10.5946(3)
_cell_measurement_reflns_used    5265
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.39
_cell_volume                     944.79(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11075
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    2.195
_exptl_absorpt_correction_T_max  0.5137
_exptl_absorpt_correction_T_min  0.4126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0355
_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)+(0.0532P)²+0.6101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                2824
_reflns_number_total             3314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01703_si_001.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4037201
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 0.46768(4) 0.79075(3) 0.23486(4) 0.07414(17) Uani 1 1 d .
O1 O -0.0170(2) 1.5317(2) 0.3208(2) 0.0578(5) Uani 1 1 d .
O2 O -0.2098(2) 1.4100(2) 0.4454(2) 0.0505(5) Uani 1 1 d .
O3 O -0.1454(2) 1.34101(19) 0.0627(2) 0.0492(5) Uani 1 1 d .
N1 N -0.0982(2) 1.1061(2) 0.1402(2) 0.0380(5) Uani 1 1 d .
C1 C 0.0208(3) 1.0157(2) 0.1747(2) 0.0351(5) Uani 1 1 d .
C2 C 0.0321(3) 0.8733(3) 0.2103(3) 0.0418(6) Uani 1 1 d .
H2A H -0.0482 0.8235 0.2207 0.050 Uiso 1 1 calc R
C3 C 0.1659(3) 0.8067(3) 0.2300(3) 0.0442(6) Uani 1 1 d .
H3A H 0.1766 0.7111 0.2532 0.053 Uiso 1 1 calc R
C4 C 0.2835(3) 0.8826(3) 0.2151(3) 0.0410(6) Uani 1 1 d .
C5 C 0.2721(3) 1.0252(2) 0.1821(3) 0.0362(5) Uani 1 1 d .
H5A H 0.3524 1.0747 0.1724 0.043 Uiso 1 1 calc R
C6 C 0.1389(3) 1.0914(2) 0.1640(2) 0.0324(5) Uani 1 1 d .
C7 C 0.0955(2) 1.2440(2) 0.1153(2) 0.0318(5) Uani 1 1 d .
C8 C -0.0638(3) 1.2413(3) 0.1014(3) 0.0361(5) Uani 1 1 d .
C9 C 0.1832(3) 1.3193(3) -0.0272(3) 0.0406(6) Uani 1 1 d .
H9A H 0.1806 1.2695 -0.0871 0.061 Uiso 1 1 calc R
H9B H 0.2818 1.3242 -0.0187 0.061 Uiso 1 1 calc R
H9C H 0.1421 1.4113 -0.0650 0.061 Uiso 1 1 calc R
C10 C -0.2417(3) 1.0635(3) 0.1439(3) 0.0513(7) Uani 1 1 d .
H10A H -0.3051 1.1439 0.1157 0.077 Uiso 1 1 calc R
H10B H -0.2796 1.0049 0.2360 0.077 Uiso 1 1 calc R
H10C H -0.2349 1.0136 0.0825 0.077 Uiso 1 1 calc R
C11 C 0.2819(3) 1.2056(3) 0.3731(3) 0.0452(6) Uani 1 1 d .
H11A H 0.2134 1.1405 0.4269 0.054 Uiso 1 1 calc R
C12 C 0.4167(4) 1.1950(4) 0.4097(4) 0.0611(8) Uani 1 1 d .
H12A H 0.4383 1.1235 0.4883 0.073 Uiso 1 1 calc R
C13 C 0.5189(3) 1.2900(4) 0.3302(4) 0.0712(10) Uani 1 1 d .
H13A H 0.6099 1.2821 0.3543 0.085 Uiso 1 1 calc R
C14 C 0.4868(3) 1.3960(4) 0.2157(4) 0.0667(9) Uani 1 1 d .
H14A H 0.5564 1.4597 0.1617 0.080 Uiso 1 1 calc R
C15 C 0.3505(3) 1.4090(3) 0.1796(3) 0.0494(7) Uani 1 1 d .
H15A H 0.3285 1.4831 0.1031 0.059 Uiso 1 1 calc R
C16 C 0.2476(2) 1.3125(2) 0.2567(3) 0.0339(5) Uani 1 1 d .
C17 C 0.1000(2) 1.3259(2) 0.2127(2) 0.0306(5) Uani 1 1 d .
H17A H 0.0874 1.4238 0.1562 0.037 Uiso 1 1 calc R
C18 C -0.0231(2) 1.2986(2) 0.3342(2) 0.0311(5) Uani 1 1 d .
C19 C -0.0801(3) 1.4259(2) 0.3650(2) 0.0346(5) Uani 1 1 d .
C20 C -0.2718(4) 1.5297(3) 0.4786(4) 0.0625(8) Uani 1 1 d .
H20A H -0.3645 1.5080 0.5368 0.094 Uiso 1 1 calc R
H20B H -0.2835 1.6056 0.3952 0.094 Uiso 1 1 calc R
H20C H -0.2085 1.5547 0.5257 0.094 Uiso 1 1 calc R
C21 C -0.0774(3) 1.1772(3) 0.4123(3) 0.0415(6) Uani 1 1 d .
H21C H -0.1514 1.1706 0.4868 0.050 Uiso 1 1 calc R
H21A H -0.0417 1.0983 0.3929 0.050 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
C19 O2 C20 115.7(2)
C8 N1 C1 111.57(19)
C8 N1 C10 123.6(2)
C1 N1 C10 124.8(2)
C2 C1 N1 129.0(2)
C2 C1 C6 121.5(2)
N1 C1 C6 109.5(2)
C1 C2 C3 118.4(2)
C1 C2 H2A 120.8
C3 C2 H2A 120.8
C4 C3 C2 119.8(2)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 122.0(2)
C3 C4 Br1 119.20(19)
C5 C4 Br1 118.75(19)
C6 C5 C4 118.3(2)
C6 C5 H5A 120.9
C4 C5 H5A 120.9
C5 C6 C1 119.9(2)
C5 C6 C7 130.6(2)
C1 C6 C7 109.1(2)
C6 C7 C9 110.18(19)
C6 C7 C8 101.59(18)
C9 C7 C8 109.10(19)
C6 C7 C17 118.22(19)
C9 C7 C17 109.23(18)
C8 C7 C17 108.00(19)
O3 C8 N1 125.4(2)
O3 C8 C7 126.4(2)
N1 C8 C7 108.2(2)
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C16 120.6(3)
C12 C11 H11A 119.7
C16 C11 H11A 119.7
C13 C12 C11 120.1(3)
C13 C12 H12A 120.0
C11 C12 H12A 120.0
C14 C13 C12 120.0(3)
C14 C13 H13A 120.0
C12 C13 H13A 120.0
C13 C14 C15 120.3(3)
C13 C14 H14A 119.9
C15 C14 H14A 119.9
C16 C15 C14 120.4(3)
C16 C15 H15A 119.8
C14 C15 H15A 119.8
C15 C16 C11 118.5(2)
C15 C16 C17 119.7(2)
C11 C16 C17 121.8(2)
C18 C17 C16 111.95(19)
C18 C17 C7 114.77(18)
C16 C17 C7 112.94(18)
C18 C17 H17A 105.4
C16 C17 H17A 105.4
C7 C17 H17A 105.4
C21 C18 C19 120.3(2)
C21 C18 C17 126.4(2)
C19 C18 C17 113.31(19)
O1 C19 O2 123.4(2)
O1 C19 C18 123.8(2)
O2 C19 C18 112.8(2)
O2 C20 H20A 109.5
O2 C20 H20B 109.5
H20A C20 H20B 109.5
O2 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C18 C21 H21C 120.0
C18 C21 H21A 120.0
H21C C21 H21A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.897(3)
O1 C19 1.199(3)
O2 C19 1.332(3)
O2 C20 1.446(3)
O3 C8 1.212(3)
N1 C8 1.369(3)
N1 C1 1.396(3)
N1 C10 1.458(3)
C1 C2 1.383(3)
C1 C6 1.397(3)
C2 C3 1.385(4)
C2 H2A 0.9300
C3 C4 1.382(4)
C3 H3A 0.9300
C4 C5 1.389(3)
C5 C6 1.375(3)
C5 H5A 0.9300
C6 C7 1.512(3)
C7 C9 1.533(3)
C7 C8 1.541(3)
C7 C17 1.570(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.382(4)
C11 C16 1.388(4)
C11 H11A 0.9300
C12 C13 1.374(5)
C12 H12A 0.9300
C13 C14 1.364(5)
C13 H13A 0.9300
C14 C15 1.390(4)
C14 H14A 0.9300
C15 C16 1.382(4)
C15 H15A 0.9300
C16 C17 1.529(3)
C17 C18 1.515(3)
C17 H17A 0.9800
C18 C21 1.321(3)
C18 C19 1.495(3)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 H21C 0.9300
C21 H21A 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 N1 C1 C2 -175.6(3)
C10 N1 C1 C2 4.1(4)
C8 N1 C1 C6 2.3(3)
C10 N1 C1 C6 -178.0(2)
N1 C1 C2 C3 175.0(2)
C6 C1 C2 C3 -2.6(4)
C1 C2 C3 C4 0.5(4)
C2 C3 C4 C5 0.8(4)
C2 C3 C4 Br1 -177.3(2)
C3 C4 C5 C6 0.0(4)
Br1 C4 C5 C6 178.13(18)
C4 C5 C6 C1 -2.1(4)
C4 C5 C6 C7 -173.5(2)
C2 C1 C6 C5 3.4(4)
N1 C1 C6 C5 -174.6(2)
C2 C1 C6 C7 176.5(2)
N1 C1 C6 C7 -1.5(3)
C5 C6 C7 C9 56.9(3)
C1 C6 C7 C9 -115.2(2)
C5 C6 C7 C8 172.4(2)
C1 C6 C7 C8 0.3(2)
C5 C6 C7 C17 -69.7(3)
C1 C6 C7 C17 118.2(2)
C1 N1 C8 O3 177.9(2)
C10 N1 C8 O3 -1.8(4)
C1 N1 C8 C7 -2.1(3)
C10 N1 C8 C7 178.2(2)
C6 C7 C8 O3 -178.9(2)
C9 C7 C8 O3 -62.6(3)
C17 C7 C8 O3 56.1(3)
C6 C7 C8 N1 1.1(2)
C9 C7 C8 N1 117.4(2)
C17 C7 C8 N1 -124.0(2)
C16 C11 C12 C13 -0.5(5)
C11 C12 C13 C14 0.8(5)
C12 C13 C14 C15 0.5(5)
C13 C14 C15 C16 -2.0(5)
C14 C15 C16 C11 2.2(4)
C14 C15 C16 C17 -178.0(3)
C12 C11 C16 C15 -1.0(4)
C12 C11 C16 C17 179.3(2)
C15 C16 C17 C18 -137.0(2)
C11 C16 C17 C18 42.8(3)
C15 C16 C17 C7 91.6(3)
C11 C16 C17 C7 -88.6(3)
C6 C7 C17 C18 -75.3(3)
C9 C7 C17 C18 157.7(2)
C8 C7 C17 C18 39.1(3)
C6 C7 C17 C16 54.6(3)
C9 C7 C17 C16 -72.4(2)
C8 C7 C17 C16 169.09(18)
C16 C17 C18 C21 -88.8(3)
C7 C17 C18 C21 41.7(3)
C16 C17 C18 C19 89.3(2)
C7 C17 C18 C19 -140.2(2)
C20 O2 C19 O1 -0.5(4)
C20 O2 C19 C18 -179.6(2)
C21 C18 C19 O1 162.4(3)
C17 C18 C19 O1 -15.9(3)
C21 C18 C19 O2 -18.5(3)
C17 C18 C19 O2 163.3(2)
