#------------------------------------------------------------------------------
#$Date: 2020-05-05 22:48:44 +0300 (Tue, 05 May 2020) $
#$Revision: 251750 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/76/4517641.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_4517641
loop_
_publ_author_name
'Jadhav, Prakash D.'
'Chen, Jia-Xuan'
'Liu, Rai-Shung'
_publ_section_title
;
 Gold(I)-Catalyzed Highly Enantioselective [4 + 2]-Annulations of
 Cyclopentadienes with Nitrosoarenes via Nitroso-Povarov versus Oxidative
 Nitroso-Povarov Reactions
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5840
_journal_paper_doi               10.1021/acscatal.0c01293
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H16 Br N O2'
_chemical_formula_weight         370.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 99.293(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4745(5)
_cell_length_b                   6.9054(5)
_cell_length_c                   18.0777(14)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3616
_cell_measurement_theta_min      3.1633
_cell_volume                     797.63(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6224
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         1.141
_exptl_absorpt_coefficient_mu    2.586
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+0.3212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0661
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                2849
_reflns_number_total             2961
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c01293_si_003.cif
_cod_data_source_block           191224LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4517641
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.04391(5) 0.24985(8) 1.16284(2) 0.02261(12) Uani 1 1 d . . . . .
O1 O 0.5133(4) -0.0933(4) 0.72002(15) 0.0184(6) Uani 1 1 d . . . . .
O2 O 0.7875(5) 0.5258(5) 0.50787(16) 0.0269(7) Uani 1 1 d . . . . .
N1 N 0.5989(5) -0.1058(5) 0.65454(18) 0.0193(7) Uani 1 1 d . . . . .
C1 C 0.8898(5) 0.2301(8) 1.06461(18) 0.0182(8) Uani 1 1 d . . . . .
C2 C 0.9890(6) 0.2886(6) 1.0058(2) 0.0197(10) Uani 1 1 d . . . . .
H16 H 1.1284 0.3362 1.0152 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8822(6) 0.2769(7) 0.93318(19) 0.0179(9) Uani 1 1 d . . . . .
H2 H 0.9503 0.3167 0.8929 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6769(6) 0.2082(5) 0.9175(2) 0.0157(9) Uani 1 1 d . . . . .
C5 C 0.5683(6) 0.1992(5) 0.8396(2) 0.0161(9) Uani 1 1 d . . . . .
C6 C 0.6129(6) 0.3014(5) 0.7820(2) 0.0173(9) Uani 1 1 d . . . . .
H5 H 0.7270 0.3891 0.7853 0.021 Uiso 1 1 calc R U . . .
C7 C 0.4616(5) 0.2627(9) 0.71076(17) 0.0153(8) Uani 1 1 d . . . . .
C8 C 0.5697(4) 0.2466(9) 0.64234(16) 0.0143(6) Uani 1 1 d . . . . .
C9 C 0.6272(7) 0.4010(7) 0.6053(3) 0.0182(10) Uani 1 1 d . . . . .
H10 H 0.5979 0.5269 0.6220 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7342(7) 0.3821(8) 0.5394(3) 0.0200(10) Uani 1 1 d . . . . .
C11 C 0.7688(6) 0.1854(7) 0.5147(2) 0.0227(11) Uani 1 1 d . . . . .
H1 H 0.8289 0.1672 0.4706 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5835(6) 0.1454(6) 0.9783(2) 0.0169(8) Uani 1 1 d . . . . .
H4 H 0.4457 0.0938 0.9690 0.020 Uiso 1 1 calc R U . . .
C13 C 0.6885(6) 0.1570(6) 1.0518(2) 0.0174(8) Uani 1 1 d . . . . .
H3 H 0.6228 0.1154 1.0924 0.021 Uiso 1 1 calc R U . . .
C14 C 0.3816(6) 0.0691(6) 0.8145(2) 0.0176(9) Uani 1 1 d . . . . .
H15 H 0.2526 0.1235 0.8291 0.021 Uiso 1 1 calc R U . . .
H14 H 0.4052 -0.0625 0.8359 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3680(7) 0.0661(6) 0.7289(2) 0.0163(9) Uani 1 1 d . . . . .
C16 C 0.6202(7) 0.0536(6) 0.6186(3) 0.0150(10) Uani 1 1 d . . . . .
C17 C 0.2946(7) 0.4233(7) 0.6993(2) 0.0223(10) Uani 1 1 d . . . . .
H7 H 0.2157 0.4223 0.7412 0.033 Uiso 1 1 calc R U . . .
H6 H 0.1989 0.4005 0.6523 0.033 Uiso 1 1 calc R U . . .
H8 H 0.3630 0.5493 0.6971 0.033 Uiso 1 1 calc R U . . .
C18 C 0.7187(7) 0.0307(7) 0.5520(3) 0.0218(10) Uani 1 1 d . . . . .
H9 H 0.7472 -0.0953 0.5352 0.026 Uiso 1 1 calc R U . . .
C19 C 0.1572(6) 0.0152(7) 0.6831(2) 0.0227(9) Uani 1 1 d . . . . .
H11 H 0.1668 0.0211 0.6296 0.034 Uiso 1 1 calc R U . . .
H13 H 0.0515 0.1076 0.6943 0.034 Uiso 1 1 calc R U . . .
H12 H 0.1173 -0.1160 0.6959 0.034 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C15 119.3(3) . . ?
C16 N1 O1 117.6(3) . . ?
C13 C1 C2 121.2(3) . . ?
C13 C1 Br1 121.5(3) . . ?
C2 C1 Br1 117.3(3) . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H16 120.4 . . ?
C1 C2 H16 120.4 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H2 119.1 . . ?
C4 C3 H2 119.1 . . ?
C3 C4 C12 117.5(3) . . ?
C3 C4 C5 120.1(3) . . ?
C12 C4 C5 122.4(3) . . ?
C6 C5 C4 126.7(3) . . ?
C6 C5 C14 110.1(3) . . ?
C4 C5 C14 123.1(3) . . ?
C5 C6 C7 112.4(3) . . ?
C5 C6 H5 123.8 . . ?
C7 C6 H5 123.8 . . ?
C6 C7 C8 112.7(3) . . ?
C6 C7 C17 109.4(4) . . ?
C8 C7 C17 110.4(4) . . ?
C6 C7 C15 101.4(3) . . ?
C8 C7 C15 110.9(4) . . ?
C17 C7 C15 111.8(3) . . ?
C9 C8 C16 119.1(3) . . ?
C9 C8 C7 123.3(5) . . ?
C16 C8 C7 117.6(5) . . ?
C8 C9 C10 122.4(4) . . ?
C8 C9 H10 118.8 . . ?
C10 C9 H10 118.8 . . ?
O2 C10 C11 123.0(4) . . ?
O2 C10 C9 120.6(5) . . ?
C11 C10 C9 116.4(4) . . ?
C18 C11 C10 122.0(4) . . ?
C18 C11 H1 119.0 . . ?
C10 C11 H1 119.0 . . ?
C13 C12 C4 121.5(4) . . ?
C13 C12 H4 119.2 . . ?
C4 C12 H4 119.2 . . ?
C1 C13 C12 118.8(3) . . ?
C1 C13 H3 120.6 . . ?
C12 C13 H3 120.6 . . ?
C5 C14 C15 102.9(3) . . ?
C5 C14 H15 111.2 . . ?
C15 C14 H15 111.2 . . ?
C5 C14 H14 111.2 . . ?
C15 C14 H14 111.2 . . ?
H15 C14 H14 109.1 . . ?
O1 C15 C19 107.5(3) . . ?
O1 C15 C14 100.7(3) . . ?
C19 C15 C14 116.9(3) . . ?
O1 C15 C7 110.8(3) . . ?
C19 C15 C7 115.9(3) . . ?
C14 C15 C7 104.0(3) . . ?
N1 C16 C8 125.6(4) . . ?
N1 C16 C18 114.7(4) . . ?
C8 C16 C18 119.5(4) . . ?
C7 C17 H7 109.5 . . ?
C7 C17 H6 109.5 . . ?
H7 C17 H6 109.5 . . ?
C7 C17 H8 109.5 . . ?
H7 C17 H8 109.5 . . ?
H6 C17 H8 109.5 . . ?
C11 C18 C16 120.4(4) . . ?
C11 C18 H9 119.8 . . ?
C16 C18 H9 119.8 . . ?
C15 C19 H11 109.5 . . ?
C15 C19 H13 109.5 . . ?
H11 C19 H13 109.5 . . ?
C15 C19 H12 109.5 . . ?
H11 C19 H12 109.5 . . ?
H13 C19 H12 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.896(3) . ?
O1 N1 1.388(4) . ?
O1 C15 1.474(5) . ?
O2 C10 1.222(6) . ?
N1 C16 1.297(6) . ?
C1 C13 1.382(6) . ?
C1 C2 1.388(5) . ?
C2 C3 1.383(5) . ?
C2 H16 0.9500 . ?
C3 C4 1.397(5) . ?
C3 H2 0.9500 . ?
C4 C12 1.405(5) . ?
C4 C5 1.471(5) . ?
C5 C6 1.327(5) . ?
C5 C14 1.516(5) . ?
C6 C7 1.511(5) . ?
C6 H5 0.9500 . ?
C7 C8 1.521(4) . ?
C7 C17 1.539(6) . ?
C7 C15 1.543(7) . ?
C8 C9 1.344(7) . ?
C8 C16 1.453(7) . ?
C9 C10 1.477(6) . ?
C9 H10 0.9500 . ?
C10 C11 1.458(7) . ?
C11 C18 1.331(7) . ?
C11 H1 0.9500 . ?
C12 C13 1.395(6) . ?
C12 H4 0.9500 . ?
C13 H3 0.9500 . ?
C14 C15 1.536(5) . ?
C14 H15 0.9900 . ?
C14 H14 0.9900 . ?
C15 C19 1.518(6) . ?
C16 C18 1.458(6) . ?
C17 H7 0.9800 . ?
C17 H6 0.9800 . ?
C17 H8 0.9800 . ?
C18 H9 0.9500 . ?
C19 H11 0.9800 . ?
C19 H13 0.9800 . ?
C19 H12 0.9800 . ?
