#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:48:51 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/53/4035323.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_4035323
loop_
_publ_author_name
'Barát, Viktor'
'Csókás, Dániel'
'Bates, Roderick W.'
_publ_section_title
;
 Synthesis of (-)-Cytisine Using a 6- endo aza-Michael Addition.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9088
_journal_page_last               9095
_journal_paper_doi               10.1021/acs.joc.8b01156
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C18 H21 Br N2 O3 S'
_chemical_formula_weight         425.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 94.832(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8775(8)
_cell_length_b                   15.4447(13)
_cell_length_c                   11.7776(10)
_cell_measurement_reflns_used    8045
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      25.6511
_cell_measurement_theta_min      2.1795
_cell_volume                     1790.3(3)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/4'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27304
_diffrn_reflns_theta_full        25.77
_diffrn_reflns_theta_max         25.77
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.588
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     238
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0592
_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)+(0.0185P)²+9.2930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                2425
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01156_si_002.cif
_cod_data_source_block           rb87s
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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_database_code               4035323
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.04866(6) 0.35506(4) 0.50869(6) 0.0346(2) Uani d . . . 1.0 . .
C C1 0.0993(5) 0.4294(3) 0.6342(5) 0.0221(13) Uani d . . . 1.0 . .
C C2 0.0296(5) 0.4236(4) 0.7294(5) 0.0266(14) Uani d . . . 1.0 . .
H H2 -0.0415 0.3827 0.7346 0.032 Uiso calc U . R 1.0 . .
C C3 0.0672(6) 0.4797(4) 0.8178(5) 0.0301(15) Uani d . . . 1.0 . .
H H3 0.0211 0.4788 0.8854 0.036 Uiso calc U . R 1.0 . .
C C4 0.1728(6) 0.5373(4) 0.8068(5) 0.0283(14) Uani d . . . 1.0 . .
H H4 0.1993 0.5767 0.8665 0.034 Uiso calc U . R 1.0 . .
C C5 0.2385(6) 0.5369(3) 0.7090(5) 0.0215(12) Uani d . . . 1.0 . .
C C6 0.3580(6) 0.5960(4) 0.6973(5) 0.0257(13) Uani d . . D 1.0 . .
H H6A 0.3698 0.6381 0.7618 0.031 Uiso calc U P R 0.297(9) A 2
H H6 0.3514 0.6426 0.7555 0.031 Uiso calc U P R 0.703(9) A 1
O O1 0.7495(7) 0.5338(4) 0.8576(5) 0.0374(19) Uani d U P D 0.703(9) A 1
H H1 0.7654 0.5747 0.9038 0.056 Uiso calc U P R 0.703(9) A 1
C C7 0.4923(8) 0.5506(6) 0.7277(8) 0.019(2) Uani d U P D 0.703(9) A 1
H H7A 0.5014 0.5015 0.6748 0.023 Uiso calc U P R 0.703(9) A 1
H H7B 0.4931 0.5268 0.8058 0.023 Uiso calc U P R 0.703(9) A 1
C C8 0.6145(10) 0.6123(6) 0.7213(8) 0.0213(19) Uani d U P D 0.703(9) A 1
H H8 0.6085 0.6582 0.7806 0.026 Uiso calc U P R 0.703(9) A 1
C C9 0.7431(11) 0.5658(8) 0.7459(9) 0.038(2) Uani d U P D 0.703(9) A 1
H H9A 0.749 0.5173 0.6915 0.045 Uiso calc U P R 0.703(9) A 1
H H9B 0.8204 0.6054 0.7373 0.045 Uiso calc U P R 0.703(9) A 1
C C10 0.6040(9) 0.6563(7) 0.6042(8) 0.019(2) Uani d U P D 0.703(9) A 1
H H10A 0.6777 0.6995 0.6012 0.022 Uiso calc U P R 0.703(9) A 1
H H10B 0.6148 0.6126 0.5442 0.022 Uiso calc U P R 0.703(9) A 1
O O1A 0.7527(14) 0.4881(7) 0.6300(10) 0.025(4) Uani d U P D 0.297(9) A 2
H H1A 0.7877 0.5093 0.5737 0.038 Uiso calc U P R 0.297(9) A 2
C C7A 0.4848(18) 0.5361(15) 0.693(2) 0.028(5) Uani d U P D 0.297(9) A 2
H H7A1 0.495 0.4991 0.7619 0.033 Uiso calc U P R 0.297(9) A 2
H H7A2 0.4736 0.498 0.6252 0.033 Uiso calc U P R 0.297(9) A 2
C C8A 0.612(2) 0.5935(15) 0.687(2) 0.029(4) Uani d U P D 0.297(9) A 2
H H8A 0.6056 0.6378 0.7484 0.035 Uiso calc U P R 0.297(9) A 2
C C9A 0.743(2) 0.5519(15) 0.713(2) 0.029(4) Uani d U P D 0.297(9) A 2
H H9A1 0.8173 0.5946 0.7095 0.035 Uiso calc U P R 0.297(9) A 2
H H9A2 0.7486 0.5258 0.7896 0.035 Uiso calc U P R 0.297(9) A 2
C C10A 0.594(2) 0.6443(19) 0.575(2) 0.027(5) Uani d U P D 0.297(9) A 2
H H10C 0.675 0.6807 0.5659 0.032 Uiso calc U P R 0.297(9) A 2
H H10D 0.581 0.6044 0.5095 0.032 Uiso calc U P R 0.297(9) A 2
C C11 0.3523(5) 0.6414(4) 0.5828(4) 0.0193(11) Uani d . . . 1.0 . .
H H11A 0.3543 0.5984 0.5207 0.023 Uiso calc U . R 1.0 . .
H H11B 0.2673 0.6754 0.5704 0.023 Uiso calc U . R 1.0 . .
C C12 0.4742(5) 0.7334(3) 0.3554(4) 0.0167(11) Uani d . . . 1.0 . .
C C13 0.5999(6) 0.7248(3) 0.3116(5) 0.0208(12) Uani d . . . 1.0 . .
H H13 0.6801 0.7445 0.354 0.025 Uiso calc U . R 1.0 . .
C C14 0.6069(6) 0.6871(4) 0.2053(5) 0.0259(13) Uani d . . . 1.0 . .
H H14 0.6924 0.6808 0.1747 0.031 Uiso calc U . R 1.0 . .
C C15 0.4897(6) 0.6587(3) 0.1435(5) 0.0262(14) Uani d . . . 1.0 . .
C C16 0.4986(8) 0.6182(4) 0.0275(5) 0.0438(18) Uani d . . . 1.0 . .
H H16A 0.4252 0.5759 0.0131 0.066 Uiso calc U . R 1.0 . .
H H16B 0.5865 0.5891 0.0253 0.066 Uiso calc U . R 1.0 . .
H H16C 0.4899 0.6634 -0.031 0.066 Uiso calc U . R 1.0 . .
C C17 0.3656(6) 0.6663(3) 0.1887(5) 0.0274(14) Uani d . . . 1.0 . .
H H17 0.2857 0.6461 0.1466 0.033 Uiso calc U . R 1.0 . .
C C18 0.3570(5) 0.7031(3) 0.2944(5) 0.0240(13) Uani d . . . 1.0 . .
H H18 0.2716 0.7078 0.3255 0.029 Uiso calc U . R 1.0 . .
N N1 0.2019(4) 0.4835(3) 0.6208(4) 0.0216(10) Uani d . . . 1.0 . .
N N2 0.4713(4) 0.6994(3) 0.5833(4) 0.0185(10) Uani d . . D 1.0 . .
O O2 0.3302(4) 0.8159(2) 0.4935(3) 0.0233(9) Uani d . . . 1.0 . .
O O3 0.5805(3) 0.8316(2) 0.5164(3) 0.0211(9) Uani d . . . 1.0 . .
S S1 0.46319(13) 0.77861(8) 0.49083(11) 0.0174(3) Uani d . . . 1.0 . .
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'
S S 0.1246 0.1234 '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
N1 C1 C2 125.4(5)
N1 C1 Br1 116.0(4)
C2 C1 Br1 118.6(4)
C1 C2 C3 117.1(5)
C2 C3 C4 119.3(5)
C5 C4 C3 119.4(6)
N1 C5 C4 122.3(5)
N1 C5 C6 117.4(5)
C4 C5 C6 120.3(5)
C5 C6 C7 112.0(6)
C5 C6 C11 113.0(5)
C7 C6 C11 113.0(5)
C5 C6 C7A 106.3(10)
C11 C6 C7A 102.4(11)
C6 C7 C8 112.0(7)
C9 C8 C10 112.7(7)
C9 C8 C7 110.8(7)
C10 C8 C7 108.9(7)
O1 C9 C8 109.1(8)
N2 C10 C8 110.0(7)
C8A C7A C6 108.6(15)
C9A C8A C10A 116.0(16)
C9A C8A C7A 116.8(16)
C10A C8A C7A 107.4(16)
O1A C9A C8A 106.4(16)
N2 C10A C8A 105.8(15)
N2 C11 C6 107.9(4)
C13 C12 C18 120.5(5)
C13 C12 S1 120.1(4)
C18 C12 S1 119.4(4)
C14 C13 C12 119.3(5)
C15 C14 C13 120.2(5)
C17 C15 C14 120.0(5)
C17 C15 C16 120.3(6)
C14 C15 C16 119.7(6)
C18 C17 C15 120.5(5)
C17 C18 C12 119.5(5)
C1 N1 C5 116.6(5)
C10 N2 C11 115.1(6)
C11 N2 C10A 107.8(14)
C10 N2 S1 116.3(5)
C11 N2 S1 117.1(3)
C10A N2 S1 112.3(10)
O3 S1 O2 119.5(2)
O3 S1 N2 107.1(2)
O2 S1 N2 106.2(2)
O3 S1 C12 108.0(2)
O2 S1 C12 107.9(2)
N2 S1 C12 107.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.906(6)
C1 N1 1.333(7)
C1 C2 1.367(8)
C2 C3 1.381(8)
C3 C4 1.385(8)
C4 C5 1.369(8)
C5 N1 1.352(7)
C5 C6 1.507(8)
C6 C7 1.517(10)
C6 C11 1.517(7)
C6 C7A 1.562(17)
O1 C9 1.402(12)
C7 C8 1.545(10)
C8 C9 1.467(10)
C8 C10 1.533(10)
C10 N2 1.472(9)
O1A C9A 1.394(19)
C7A C8A 1.543(17)
C8A C9A 1.454(16)
C8A C10A 1.532(16)
C10A N2 1.491(16)
C11 N2 1.478(6)
C12 C13 1.390(7)
C12 C18 1.391(7)
C12 S1 1.753(5)
C13 C14 1.388(7)
C14 C15 1.386(8)
C15 C17 1.381(8)
C15 C16 1.511(8)
C17 C18 1.378(8)
N2 S1 1.635(4)
O2 S1 1.437(4)
O3 S1 1.430(4)
