#------------------------------------------------------------------------------
#$Date: 2021-11-21 01:12:20 +0200 (Sun, 21 Nov 2021) $
#$Revision: 270790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565337.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_1565337
loop_
_publ_author_name
'Shen, Chong'
'Cheng, Xiang'
'Wei, Liang'
'Wang, Ruo-Qing'
'Wang, Chun-Jiang'
_publ_section_title
;
 Stereodivergent Synthesis via Iridium-Catalyzed Asymmetric Double Allylic
 Alkylation of Cyanoacetate
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06115A
_journal_year                    2021
_chemical_formula_moiety         'C25 H25 Br2 N O2'
_chemical_formula_sum            'C25 H25 Br2 N O2'
_chemical_formula_weight         531.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-14 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.4620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.982
_cell_length_b                   20.17050(10)
_cell_length_c                   9.655
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.495
_cell_measurement_theta_min      4.384
_cell_volume                     1128.058(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22395
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_min         4.384
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    4.724
_exptl_absorpt_correction_T_max  0.685
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0236P)²+0.9886P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             2083
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc06115a2.cif
_cod_data_source_block           wang1
_cod_database_code               1565337
_shelxl_version_number           2013-2
_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.
;
_shelx_estimated_absorpt_t_max   0.704
_shelx_estimated_absorpt_t_min   0.331
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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 0.42639(3) 0.55919(2) 0.16388(2) 0.02157(8) Uani 1 1 d . . . . .
O1 O 0.1201(3) 0.2500 0.16405(16) 0.0121(3) Uani 1 2 d S T P . .
O2 O 0.4845(3) 0.2500 0.30663(17) 0.0147(3) Uani 1 2 d S T P . .
N1 N 0.4627(4) 0.2500 0.6572(2) 0.0192(4) Uani 1 2 d S T P . .
C1 C 0.1544(4) 0.2500 0.4105(2) 0.0104(4) Uani 1 2 d S T P . .
C2 C 0.3317(4) 0.2500 0.5480(2) 0.0123(4) Uani 1 2 d S T P . .
C3 C 0.0032(3) 0.31550(8) 0.39729(16) 0.0113(3) Uani 1 1 d . . . . .
H3 H -0.1432 0.3063 0.3232 0.014 Uiso 1 1 calc R . . . .
C4 C -0.0661(3) 0.33179(8) 0.53416(18) 0.0164(3) Uani 1 1 d . . . . .
H4 H -0.169(4) 0.3025(11) 0.557(2) 0.029(6) Uiso 1 1 d . . . . .
C5 C -0.0054(3) 0.38440(10) 0.6145(2) 0.0221(4) Uani 1 1 d . . . . .
H5A H -0.058(4) 0.3900(11) 0.695(2) 0.025(5) Uiso 1 1 d . . . . .
H5B H 0.087(4) 0.4152(13) 0.590(3) 0.035(6) Uiso 1 1 d . . . . .
C6 C 0.1145(3) 0.37466(8) 0.34347(16) 0.0120(3) Uani 1 1 d . . . . .
C7 C 0.3443(3) 0.39284(8) 0.39907(17) 0.0145(3) Uani 1 1 d . . . . .
H7 H 0.4385 0.3674 0.4742 0.017 Uiso 1 1 calc R . . . .
C8 C 0.4379(3) 0.44759(8) 0.34621(18) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.5956 0.4590 0.3832 0.019 Uiso 1 1 calc R . . . .
C9 C 0.2980(3) 0.48507(8) 0.23909(17) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.0669(3) 0.46994(8) 0.18493(17) 0.0161(3) Uani 1 1 d . . . . .
H10 H -0.0287 0.4971 0.1138 0.019 Uiso 1 1 calc R . . . .
C11 C -0.0226(3) 0.41419(8) 0.23661(17) 0.0138(3) Uani 1 1 d . . . . .
H11 H -0.1801 0.4028 0.1985 0.017 Uiso 1 1 calc R . . . .
C12 C 0.2778(4) 0.2500 0.2877(2) 0.0113(4) Uani 1 2 d S T P . .
C13 C 0.1882(4) 0.2500 0.0248(2) 0.0145(5) Uani 1 2 d S T P . .
C14 C 0.3230(3) 0.31270(9) 0.01264(19) 0.0220(4) Uani 1 1 d . . . . .
H14A H 0.2345 0.3515 0.0292 0.033 Uiso 1 1 calc GR . . . .
H14B H 0.3497 0.3153 -0.0833 0.033 Uiso 1 1 calc GR . . . .
H14C H 0.4716 0.3117 0.0841 0.033 Uiso 1 1 calc GR . . . .
C15 C -0.0442(5) 0.2500 -0.0824(3) 0.0238(5) Uani 1 2 d S T P . .
H15A H -0.0219 0.2528 -0.1794 0.036 Uiso 0.5 1 calc GR . . A -1
H15B H -0.1346 0.2882 -0.0647 0.036 Uiso 0.5 1 calc GR . . A -1
H15C H -0.1267 0.2090 -0.0726 0.036 Uiso 0.5 1 calc GR . . A -1
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'
Br Br -0.6763 1.2805 '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'
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
C12 O1 C13 121.11(17) . . ?
C2 C1 C3 109.79(11) . 4_565 ?
C2 C1 C3 109.79(11) . . ?
C2 C1 C12 108.40(18) . . ?
C3 C1 C3 112.61(17) 4_565 . ?
C12 C1 C3 108.07(11) . . ?
C12 C1 C3 108.07(11) . 4_565 ?
N1 C2 C1 177.4(2) . . ?
C4 C3 C1 112.62(13) . . ?
C4 C3 C6 111.49(13) . . ?
C6 C3 C1 113.05(13) . . ?
C5 C4 C3 126.51(16) . . ?
C7 C6 C3 123.29(14) . . ?
C7 C6 C11 118.36(15) . . ?
C11 C6 C3 118.31(14) . . ?
C8 C7 C6 121.06(15) . . ?
C9 C8 C7 119.01(15) . . ?
C8 C9 Br1 119.23(12) . . ?
C8 C9 C10 121.54(15) . . ?
C10 C9 Br1 119.24(12) . . ?
C9 C10 C11 118.71(15) . . ?
C10 C11 C6 121.26(15) . . ?
O1 C12 C1 108.80(18) . . ?
O2 C12 O1 127.6(2) . . ?
O2 C12 C1 123.6(2) . . ?
O1 C13 C14 109.74(12) . 4_565 ?
O1 C13 C14 109.74(12) . . ?
O1 C13 C15 101.82(18) . . ?
C14 C13 C14 112.6(2) 4_565 . ?
C15 C13 C14 111.21(13) . . ?
C15 C13 C14 111.21(13) . 4_565 ?
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 C9 1.9055(16) . ?
O1 C12 1.324(3) . ?
O1 C13 1.499(3) . ?
O2 C12 1.204(3) . ?
N1 C2 1.146(3) . ?
C1 C2 1.478(3) . ?
C1 C3 1.5879(19) . ?
C1 C3 1.5878(19) 4_565 ?
C1 C12 1.545(3) . ?
C3 C4 1.517(2) . ?
C3 C6 1.520(2) . ?
C4 C5 1.311(3) . ?
C6 C7 1.394(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.391(2) . ?
C13 C14 1.520(2) . ?
C13 C14 1.520(2) 4_565 ?
C13 C15 1.512(3) . ?
