#------------------------------------------------------------------------------
#$Date: 2023-11-06 10:19:38 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159578.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_7159578
loop_
_publ_author_name
'Li, Yu'
'Wang, Mei'
'Ma, Rongrong'
'Niu, Rui'
'Wang, Haodong'
'Zhang, Yantu'
'Lin, Jun-Bing'
_publ_section_title
;
 Organocatalytic allylic alkylation of alkyne-substituted MBH carbonates:
 access to quaternary carbon-containing 1,4-enynes.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8263
_journal_page_last               8266
_journal_paper_doi               10.1039/d3ob01317k
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Br N O6'
_chemical_formula_sum            'C17 H16 Br N O6'
_chemical_formula_weight         410.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-22 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.518(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.220(3)
_cell_length_b                   27.478(9)
_cell_length_c                   8.339(3)
_cell_measurement_reflns_used    2706
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.18
_cell_measurement_theta_min      2.62
_cell_volume                     1856.3(11)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8654
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.621
_diffrn_source                   TXS
_diffrn_source_type              'Rotaing Anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1162 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.5659.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0398
_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)+(0.0087P)²+1.3494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.502
_reflns_Friedel_fraction_full    0.535
_reflns_Friedel_fraction_max     0.504
_reflns_number_gt                2255
_reflns_number_total             3197
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01317k2.cif
_cod_data_source_block           aw_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159578--7159579.cif.
;
_cod_original_cell_volume        1856.5(10)
_cod_database_code               7159578
_shelx_shelxl_version_number     2019/2
_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   0.807
_shelx_estimated_absorpt_t_min   0.759
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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 0.53882(11) 0.77391(2) 0.64782(12) 0.1095(3) Uani 1 1 d . . . . .
O2 O 0.3710(5) 0.59554(15) 0.2810(6) 0.0725(10) Uani 1 1 d . . . . .
O4 O 0.8768(5) 0.58524(14) 0.5239(6) 0.0784(11) Uani 1 1 d . . . . .
O5 O 0.6157(7) 0.58488(18) 1.0416(7) 0.1005(15) Uani 1 1 d . . . . .
O3 O 0.6880(5) 0.53053(13) 0.4976(6) 0.0812(12) Uani 1 1 d . . . . .
N1 N 0.6679(7) 0.57485(16) 0.9385(7) 0.0707(13) Uani 1 1 d . . . . .
O1 O 0.3060(5) 0.53628(15) 0.4180(6) 0.0839(12) Uani 1 1 d . . . . .
C7 C 0.3685(7) 0.67448(18) 0.6436(7) 0.0569(12) Uani 1 1 d . . . . .
C20 C 0.6687(6) 0.60977(16) 0.5922(7) 0.0533(11) Uani 1 1 d . . . . .
C10 C 0.3841(7) 0.57098(18) 0.4218(8) 0.0572(13) Uani 1 1 d . . . . .
C16 C 0.7437(6) 0.57095(19) 0.5332(8) 0.0609(13) Uani 1 1 d . . . . .
C8 C 0.4329(6) 0.63886(18) 0.6291(7) 0.0579(12) Uani 1 1 d . . . . .
O6 O 0.8119(6) 0.5782(2) 0.9736(7) 0.1091(16) Uani 1 1 d . . . . .
C1 C 0.2627(10) 0.8039(2) 0.6804(10) 0.094(2) Uani 1 1 d . . . . .
H1 H 0.305843 0.834806 0.686471 0.113 Uiso 1 1 calc R U . . .
C9 C 0.5137(6) 0.59523(14) 0.6022(7) 0.0506(11) Uani 1 1 d . . . . .
C13 C 0.5481(7) 0.55668(17) 0.7520(7) 0.0610(13) Uani 1 1 d . . . . .
H13A H 0.445121 0.548147 0.749964 0.073 Uiso 1 1 calc R U . . .
H13B H 0.592051 0.527487 0.725685 0.073 Uiso 1 1 calc R U . . .
C17 C 0.7345(8) 0.6534(2) 0.6346(10) 0.086(2) Uani 1 1 d . . . . .
H17A H 0.830198 0.660301 0.627886 0.103 Uiso 1 1 calc R U . . .
H17B H 0.685494 0.677344 0.671474 0.103 Uiso 1 1 calc R U . . .
C2 C 0.3424(8) 0.7639(2) 0.6638(9) 0.0734(16) Uani 1 1 d . . . . .
C3 C 0.2848(7) 0.71707(18) 0.6593(8) 0.0625(14) Uani 1 1 d . . . . .
C19 C 0.9567(9) 0.5485(3) 0.4695(11) 0.107(3) Uani 1 1 d . . . . .
H19A H 1.000053 0.523503 0.560769 0.160 Uiso 1 1 calc R U . . .
H19B H 1.045252 0.563085 0.456567 0.160 Uiso 1 1 calc R U . . .
H19C H 0.878089 0.534628 0.355128 0.160 Uiso 1 1 calc R U . . .
C4 C 0.1383(9) 0.7116(2) 0.6651(11) 0.090(2) Uani 1 1 d . . . . .
H4 H 0.096039 0.680583 0.659972 0.108 Uiso 1 1 calc R U . . .
C5 C 0.1186(11) 0.7980(3) 0.6879(11) 0.102(2) Uani 1 1 d . . . . .
H5 H 0.064413 0.825195 0.699420 0.122 Uiso 1 1 calc R U . . .
C6 C 0.0521(13) 0.7523(3) 0.6786(15) 0.112(3) Uani 1 1 d . . . . .
H6 H -0.047027 0.748568 0.681180 0.135 Uiso 1 1 calc R U . . .
C11 C 0.2478(10) 0.5763(3) 0.1010(9) 0.105(2) Uani 1 1 d . . . . .
H11A H 0.290414 0.547311 0.071800 0.126 Uiso 1 1 calc R U . . .
H11B H 0.147081 0.567764 0.104007 0.126 Uiso 1 1 calc R U . . .
C12 C 0.2144(11) 0.6126(3) -0.0331(11) 0.130(3) Uani 1 1 d . . . . .
H12A H 0.165844 0.640413 -0.007623 0.195 Uiso 1 1 calc R U . . .
H12B H 0.139299 0.599875 -0.151370 0.195 Uiso 1 1 calc R U . . .
H12C H 0.315453 0.622009 -0.031296 0.195 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'
Br Br -0.2901 2.4595 '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'
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
C10 O2 C11 115.0(5) . . ?
C16 O4 C19 115.9(5) . . ?
O5 N1 O6 125.0(6) . . ?
O5 N1 C13 118.0(5) . . ?
O6 N1 C13 117.0(6) . . ?
C8 C7 C3 178.1(6) . . ?
C16 C20 C9 115.4(4) . . ?
C17 C20 C16 121.3(5) . . ?
C17 C20 C9 123.3(5) . . ?
O2 C10 C9 110.2(4) . . ?
O1 C10 O2 126.6(6) . . ?
O1 C10 C9 123.1(5) . . ?
O4 C16 C20 113.5(4) . . ?
O3 C16 O4 123.9(5) . . ?
O3 C16 C20 122.5(5) . . ?
C7 C8 C9 177.0(5) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C5 119.4(6) . . ?
C5 C1 H1 120.3 . . ?
C20 C9 C10 111.5(4) . . ?
C20 C9 C13 112.8(4) . . ?
C8 C9 C20 110.4(4) . . ?
C8 C9 C10 106.4(4) . . ?
C8 C9 C13 110.7(4) . . ?
C13 C9 C10 104.7(4) . . ?
N1 C13 C9 112.0(4) . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C9 C13 H13A 109.2 . . ?
C9 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C20 C17 H17A 120.0 . . ?
C20 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C1 C2 Br1 117.9(5) . . ?
C1 C2 C3 122.2(6) . . ?
C3 C2 Br1 120.0(4) . . ?
C2 C3 C7 122.8(5) . . ?
C4 C3 C7 119.3(5) . . ?
C4 C3 C2 117.9(5) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C6 121.0(7) . . ?
C6 C4 H4 119.5 . . ?
C1 C5 H5 119.4 . . ?
C1 C5 C6 121.3(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C6 H6 120.9 . . ?
C5 C6 C4 118.2(8) . . ?
C5 C6 H6 120.9 . . ?
O2 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 O2 108.8(6) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 C2 1.899(6) . ?
O2 C10 1.309(7) . ?
O2 C11 1.481(8) . ?
O4 C16 1.326(6) . ?
O4 C19 1.444(7) . ?
O5 N1 1.201(6) . ?
O3 C16 1.200(6) . ?
N1 O6 1.219(7) . ?
N1 C13 1.499(7) . ?
O1 C10 1.186(6) . ?
C7 C8 1.181(7) . ?
C7 C3 1.442(7) . ?
C20 C16 1.478(7) . ?
C20 C9 1.524(7) . ?
C20 C17 1.313(7) . ?
C10 C9 1.555(7) . ?
C8 C9 1.484(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.365(8) . ?
C1 C5 1.369(10) . ?
C9 C13 1.551(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C2 C3 1.385(7) . ?
C3 C4 1.383(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C6 1.407(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(11) . ?
C6 H6 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.418(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C7 0.3(8) . . . . ?
Br1 C2 C3 C4 -177.8(5) . . . . ?
O2 C10 C9 C20 -44.4(5) . . . . ?
O2 C10 C9 C8 76.1(5) . . . . ?
O2 C10 C9 C13 -166.6(4) . . . . ?
O5 N1 C13 C9 107.5(5) . . . . ?
O1 C10 C9 C20 138.4(5) . . . . ?
O1 C10 C9 C8 -101.2(6) . . . . ?
O1 C10 C9 C13 16.1(7) . . . . ?
C7 C3 C4 C6 -179.4(7) . . . . ?
C20 C9 C13 N1 60.5(5) . . . . ?
C10 O2 C11 C12 164.4(7) . . . . ?
C10 C9 C13 N1 -178.1(4) . . . . ?
C16 C20 C9 C10 -51.5(5) . . . . ?
C16 C20 C9 C8 -169.6(4) . . . . ?
C16 C20 C9 C13 66.0(6) . . . . ?
C8 C9 C13 N1 -63.8(6) . . . . ?
O6 N1 C13 C9 -72.6(6) . . . . ?
C1 C2 C3 C7 -179.4(6) . . . . ?
C1 C2 C3 C4 2.4(10) . . . . ?
C1 C5 C6 C4 1.4(13) . . . . ?
C9 C20 C16 O4 179.1(5) . . . . ?
C9 C20 C16 O3 -0.9(8) . . . . ?
C17 C20 C16 O4 -1.7(8) . . . . ?
C17 C20 C16 O3 178.3(6) . . . . ?
C17 C20 C9 C10 129.4(6) . . . . ?
C17 C20 C9 C8 11.3(7) . . . . ?
C17 C20 C9 C13 -113.2(6) . . . . ?
C2 C1 C5 C6 -0.2(12) . . . . ?
C2 C3 C4 C6 -1.2(11) . . . . ?
C3 C4 C6 C5 -0.7(13) . . . . ?
C19 O4 C16 O3 -0.9(9) . . . . ?
C19 O4 C16 C20 179.1(5) . . . . ?
C5 C1 C2 Br1 178.5(6) . . . . ?
C5 C1 C2 C3 -1.8(11) . . . . ?
C11 O2 C10 O1 -1.5(9) . . . . ?
C11 O2 C10 C9 -178.7(5) . . . . ?
