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#$Date: 2020-05-29 02:24:37 +0300 (Fri, 29 May 2020) $
#$Revision: 252446 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038428.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_4038428
loop_
_publ_author_name
'Magnus, Nicholas Andrew'
'Buser, Jonas Y.'
'Embry, Matthew C.'
'Kallman, Neil John'
_publ_section_title
;
 Diastereoselective Pictet-Spengler Based Synthesis of a Chiral
 Tetrahydroisoquinoline D1 Potentiator.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00177
_journal_year                    2020
_chemical_formula_sum            'C18 H18 Br N O4 S'
_chemical_formula_weight         424.30
_chemical_name_systematic        LSN3495203
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.348(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5479(16)
_cell_length_b                   5.7655(9)
_cell_length_c                   14.537(2)
_cell_measurement_reflns_used    8561
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.26
_cell_measurement_theta_min      3.24
_cell_volume                     907.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX3 CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11348
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.467
_diffrn_reflns_theta_min         3.242
_exptl_absorpt_coefficient_mu    4.361
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       rod
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_transmission_factor_max   0.7536
_exptl_transmission_factor_min   0.5396
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.259
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1583P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2253
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                3067
_reflns_number_total             3314
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00177_si_001.cif
_cod_data_source_block           compound_8
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038428
_elnb_number
;
RP7-H81584-086
;
_lot_number
;
RP7-H80584-086
;
_comments
;

;
_shelx_shelxl_version_number     2014/7
_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_min   0.561
_shelx_estimated_absorpt_t_max   0.958
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
Br01 Br 0.78402(10) 0.8366(2) 0.25973(8) 0.0635(5) Uani 1 1 d . . . . .
S1 S 0.31082(19) 0.4721(4) 0.06699(13) 0.0441(6) Uani 1 1 d . . . . .
O003 O 0.4242(6) 0.3254(14) 0.3881(4) 0.0502(14) Uani 1 1 d . . . . .
O004 O 0.3402(8) 0.0422(13) 0.2803(5) 0.065(2) Uani 1 1 d . . . . .
O005 O 0.3559(7) 0.7063(13) 0.0855(5) 0.0571(16) Uani 1 1 d . . . . .
O006 O 0.2744(7) 0.3835(15) -0.0312(5) 0.0626(19) Uani 1 1 d . . . . .
N007 N 0.4555(6) 0.3373(13) 0.2469(5) 0.0410(13) Uani 1 1 d . . . . .
C21 C 0.1848(7) 0.4443(15) 0.1076(6) 0.0429(17) Uani 1 1 d . . . . .
C9 C 0.4744(8) 0.5527(15) 0.3817(6) 0.0445(18) Uani 1 1 d . . . . .
C6 C 0.7549(7) 0.6003(16) 0.4229(6) 0.0440(17) Uani 1 1 d . . . . .
C26 C 0.1571(8) 0.6240(15) 0.1605(6) 0.0471(19) Uani 1 1 d . . . . .
C1 C 0.8085(7) 0.7891(16) 0.3943(7) 0.050(2) Uani 1 1 d . . . . .
C10 C 0.4003(8) 0.2176(16) 0.3009(6) 0.0456(18) Uani 1 1 d . . . . .
C7 C 0.6705(7) 0.4280(15) 0.3523(6) 0.0447(18) Uani 1 1 d . . . . .
H7A H 0.6694 0.2847 0.3870 0.054 Uiso 1 1 calc R U . . .
H7B H 0.7030 0.3935 0.3007 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4312(8) 0.2806(15) 0.1458(6) 0.0450(19) Uani 1 1 d . . . . .
C8 C 0.5373(7) 0.5198(13) 0.3060(6) 0.0385(16) Uani 1 1 d . . . . .
C5 C 0.7796(8) 0.5720(19) 0.5230(7) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.7467 0.4449 0.5448 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5428(10) 0.303(2) 0.1114(7) 0.065(3) Uani 1 1 d . . . . .
H12A H 0.5801 0.4525 0.1293 0.097 Uiso 1 1 calc R U . . .
H12B H 0.5157 0.2847 0.0415 0.097 Uiso 1 1 calc R U . . .
H12C H 0.6022 0.1843 0.1421 0.097 Uiso 1 1 calc R U . . .
C22 C 0.1103(9) 0.2473(17) 0.0834(7) 0.052(2) Uani 1 1 d . . . . .
H22 H 0.1300 0.1260 0.0493 0.062 Uiso 1 1 calc R U . . .
C25 C 0.0536(10) 0.606(2) 0.1878(8) 0.057(2) Uani 1 1 d . . . . .
C2 C 0.8817(8) 0.946(2) 0.4612(8) 0.058(2) Uani 1 1 d . . . . .
H2 H 0.9174 1.0703 0.4399 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8524(9) 0.730(3) 0.5912(8) 0.066(3) Uani 1 1 d . . . . .
H4 H 0.8675 0.7080 0.6577 0.079 Uiso 1 1 calc R U . . .
C24 C -0.0203(9) 0.413(2) 0.1625(8) 0.061(3) Uani 1 1 d . . . . .
H24 H -0.0898 0.4029 0.1806 0.073 Uiso 1 1 calc R U . . .
C23 C 0.0074(9) 0.234(2) 0.1102(7) 0.058(3) Uani 1 1 d . . . . .
H23 H -0.0436 0.1042 0.0933 0.070 Uiso 1 1 calc R U . . .
C3 C 0.9016(9) 0.918(2) 0.5606(8) 0.063(3) Uani 1 1 d . . . . .
H3 H 0.9482 1.0262 0.6059 0.076 Uiso 1 1 calc R U . . .
H8 H 0.534(8) 0.639(17) 0.265(7) 0.03(2) Uiso 1 1 d . . . . .
H11 H 0.390(9) 0.122(19) 0.134(7) 0.04(2) Uiso 1 1 d . . . . .
H9A H 0.527(8) 0.590(17) 0.445(7) 0.04(2) Uiso 1 1 d . . . . .
H9B H 0.404(10) 0.66(2) 0.367(8) 0.05(3) Uiso 1 1 d . . . . .
H25 H 0.028(11) 0.73(2) 0.221(8) 0.06(3) Uiso 1 1 d . . . . .
H26 H 0.215(8) 0.771(16) 0.168(6) 0.03(2) Uiso 1 1 d . . . . .
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'
S S 0.3331 0.5567 '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
O006 S1 O005 118.8(5) . . ?
O006 S1 C21 108.2(4) . . ?
O005 S1 C21 108.1(4) . . ?
O006 S1 C11 107.7(4) . . ?
O005 S1 C11 107.6(4) . . ?
C21 S1 C11 105.8(4) . . ?
C10 O003 C9 108.2(7) . . ?
C10 N007 C11 120.8(7) . . ?
C10 N007 C8 111.1(6) . . ?
C11 N007 C8 128.1(7) . . ?
C22 C21 C26 120.4(9) . . ?
C22 C21 S1 120.0(7) . . ?
C26 C21 S1 119.6(7) . . ?
O003 C9 C8 103.6(6) . . ?
O003 C9 H9A 107(6) . . ?
C8 C9 H9A 115(6) . . ?
O003 C9 H9B 106(7) . . ?
C8 C9 H9B 119(7) . . ?
H9A C9 H9B 105(8) . . ?
C1 C6 C5 117.1(8) . . ?
C1 C6 C7 124.1(8) . . ?
C5 C6 C7 118.7(8) . . ?
C25 C26 C21 119.2(9) . . ?
C25 C26 H26 128(5) . . ?
C21 C26 H26 113(5) . . ?
C2 C1 C6 122.1(10) . . ?
C2 C1 Br01 117.8(8) . . ?
C6 C1 Br01 120.1(7) . . ?
O004 C10 O003 122.2(9) . . ?
O004 C10 N007 128.9(9) . . ?
O003 C10 N007 108.9(7) . . ?
C6 C7 C8 112.3(6) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N007 C11 C12 115.2(7) . . ?
N007 C11 S1 109.8(6) . . ?
C12 C11 S1 106.6(6) . . ?
N007 C11 H11 107(6) . . ?
C12 C11 H11 115(6) . . ?
S1 C11 H11 103(5) . . ?
N007 C8 C9 98.0(6) . . ?
N007 C8 C7 110.4(6) . . ?
C9 C8 C7 112.3(7) . . ?
N007 C8 H8 106(6) . . ?
C9 C8 H8 117(6) . . ?
C7 C8 H8 111(6) . . ?
C6 C5 C4 121.4(10) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C23 C22 C21 119.5(10) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C25 C26 120.1(10) . . ?
C24 C25 H25 118(7) . . ?
C26 C25 H25 122(7) . . ?
C1 C2 C3 119.6(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C3 C4 C5 120.2(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C25 C24 C23 120.8(10) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C22 C23 C24 120.0(9) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C4 C3 C2 119.6(10) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
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
Br01 C1 1.896(10) . ?
S1 O006 1.435(7) . ?
S1 O005 1.438(8) . ?
S1 C21 1.758(9) . ?
S1 C11 1.832(8) . ?
O003 C10 1.351(11) . ?
O003 C9 1.448(12) . ?
O004 C10 1.203(12) . ?
N007 C10 1.360(12) . ?
N007 C11 1.435(10) . ?
N007 C8 1.474(10) . ?
C21 C22 1.394(12) . ?
C21 C26 1.392(12) . ?
C9 C8 1.527(12) . ?
C9 H9A 0.93(9) . ?
C9 H9B 1.00(12) . ?
C6 C1 1.386(14) . ?
C6 C5 1.391(13) . ?
C6 C7 1.514(11) . ?
C26 C25 1.387(14) . ?
C26 H26 1.06(9) . ?
C1 C2 1.383(14) . ?
C7 C8 1.543(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 C12 1.541(14) . ?
C11 H11 1.02(11) . ?
C8 H8 0.90(10) . ?
C5 C4 1.394(15) . ?
C5 H5 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C22 C23 1.376(15) . ?
C22 H22 0.9300 . ?
C25 C24 1.371(16) . ?
C25 H25 0.97(14) . ?
C2 C3 1.391(16) . ?
C2 H2 0.9300 . ?
C4 C3 1.368(19) . ?
C4 H4 0.9300 . ?
C24 C23 1.385(18) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C3 H3 0.9300 . ?
