#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:55:29 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/54/1555437.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_1555437
loop_
_publ_author_name
'Yang, Van-Wei'
'Hong, Bor-Cherng'
'Kao, Hsin-Kai'
'Tu, Ting-Hsun'
'Shen, Jiun-Yi'
'Chen, Chi-Lin'
'Lee, Gene-Hsiang'
'Chou, Pi-Tai'
_publ_section_title
;
 One-Pot Dichotomous Construction of Inside-Azayohimban and
 Pro-Azayohimban Systems via an Enantioselective Organocatalytic Cascade;
 Their Use as a Model to Probe the (Aza-)Indole Local Solvent Environment.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5816
_journal_page_last               5819
_journal_paper_doi               10.1021/acs.orglett.5b02949
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H28 N4 O5'
_chemical_formula_weight         464.51
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2785(2)
_cell_length_b                   9.2956(2)
_cell_length_c                   29.7576(7)
_cell_measurement_reflns_used    12020
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.37
_cell_volume                     2289.96(9)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12020
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.8(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2536
_reflns_number_total             4001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02949_si_003.cif
_cod_data_source_block           ic16940
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1555437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.5107(2) -0.1140(2) 0.16979(7) 0.0469(6) Uani 1 1 d .
O2 O 0.7761(3) 0.1410(3) -0.02545(9) 0.0854(9) Uani 1 1 d .
O3 O 0.7011(3) -0.0354(3) 0.01679(9) 0.0714(8) Uani 1 1 d .
O4 O 0.5605(3) 0.5474(2) 0.11339(7) 0.0552(7) Uani 1 1 d .
O5 O 0.8314(3) 0.7960(3) 0.13782(10) 0.0656(8) Uani 1 1 d .
H5A H 0.861(5) 0.714(4) 0.1341(14) 0.098 Uiso 1 1 d .
H5B H 0.730(5) 0.790(5) 0.1368(14) 0.098 Uiso 1 1 d .
N1 N 1.2614(3) -0.0151(2) 0.16975(8) 0.0316(6) Uani 1 1 d .
N2 N 1.0526(3) 0.3363(2) 0.15751(7) 0.0331(6) Uani 1 1 d .
H2 H 0.9880 0.3414 0.1341 0.040 Uiso 1 1 calc R
N3 N 1.0191(3) 0.5775(3) 0.18428(8) 0.0370(6) Uani 1 1 d .
N4 N 0.8008(4) 0.0512(4) 0.00380(10) 0.0528(8) Uani 1 1 d .
C1 C 1.3934(4) -0.0671(3) 0.14831(10) 0.0358(8) Uani 1 1 d .
C2 C 1.3881(3) -0.0721(3) 0.09834(9) 0.0370(8) Uani 1 1 d .
H2A H 1.4461 -0.1589 0.0878 0.044 Uiso 1 1 calc R
H2B H 1.4445 0.0132 0.0861 0.044 Uiso 1 1 calc R
C3 C 1.2168(3) -0.0752(3) 0.08071(9) 0.0320(7) Uani 1 1 d .
H3 H 1.1598 -0.1594 0.0943 0.038 Uiso 1 1 calc R
C4 C 1.2182(4) -0.0940(3) 0.03011(9) 0.0410(8) Uani 1 1 d .
H4A H 1.2804 -0.0146 0.0163 0.049 Uiso 1 1 calc R
H4B H 1.2728 -0.1856 0.0225 0.049 Uiso 1 1 calc R
C5 C 1.0485(4) -0.0951(3) 0.01104(10) 0.0413(8) Uani 1 1 d .
H5C H 1.0521 -0.1046 -0.0221 0.050 Uiso 1 1 calc R
H5D H 0.9867 -0.1772 0.0234 0.050 Uiso 1 1 calc R
C6 C 0.9688(3) 0.0456(3) 0.02410(9) 0.0371(8) Uani 1 1 d .
H6 H 1.0341 0.1269 0.0117 0.045 Uiso 1 1 calc R
C7 C 0.9552(3) 0.0636(3) 0.07564(9) 0.0313(7) Uani 1 1 d .
H7 H 0.8982 -0.0232 0.0876 0.038 Uiso 1 1 calc R
C8 C 1.1296(3) 0.0632(3) 0.09566(8) 0.0297(7) Uani 1 1 d .
H8 H 1.1900 0.1483 0.0838 0.036 Uiso 1 1 calc R
C9 C 1.1286(3) 0.0697(3) 0.14817(8) 0.0289(7) Uani 1 1 d .
H9 H 1.0244 0.0262 0.1583 0.035 Uiso 1 1 calc R
C10 C 1.1409(3) 0.2166(3) 0.17020(9) 0.0300(7) Uani 1 1 d .
C11 C 1.2280(3) 0.2489(3) 0.20850(9) 0.0306(7) Uani 1 1 d .
C12 C 1.3230(4) 0.1398(3) 0.23403(9) 0.0372(8) Uani 1 1 d .
H12A H 1.3062 0.1523 0.2667 0.045 Uiso 1 1 calc R
H12B H 1.4397 0.1504 0.2275 0.045 Uiso 1 1 calc R
C13 C 1.2637(4) -0.0073(3) 0.21909(9) 0.0357(8) Uani 1 1 d .
H13A H 1.3359 -0.0829 0.2312 0.043 Uiso 1 1 calc R
H13B H 1.1536 -0.0243 0.2310 0.043 Uiso 1 1 calc R
C14 C 1.0820(3) 0.4454(3) 0.18727(9) 0.0294(7) Uani 1 1 d .
C15 C 1.1917(3) 0.3953(3) 0.21976(9) 0.0301(7) Uani 1 1 d .
C16 C 1.2351(4) 0.4904(3) 0.25401(10) 0.0361(8) Uani 1 1 d .
H16 H 1.3061 0.4624 0.2775 0.043 Uiso 1 1 calc R
C17 C 1.1700(4) 0.6272(3) 0.25210(10) 0.0382(8) Uani 1 1 d .
H17 H 1.1963 0.6956 0.2747 0.046 Uiso 1 1 calc R
C18 C 1.0663(4) 0.6651(3) 0.21735(11) 0.0384(8) Uani 1 1 d .
H18 H 1.0259 0.7608 0.2171 0.046 Uiso 1 1 calc R
C19 C 0.8518(3) 0.1927(3) 0.08634(9) 0.0309(7) Uani 1 1 d .
C20 C 0.7234(4) 0.1802(3) 0.11618(9) 0.0358(8) Uani 1 1 d .
H20 H 0.7037 0.0900 0.1302 0.043 Uiso 1 1 calc R
C21 C 0.6237(4) 0.2949(3) 0.12605(10) 0.0405(8) Uani 1 1 d .
H21 H 0.5358 0.2827 0.1462 0.049 Uiso 1 1 calc R
C22 C 0.6516(4) 0.4274(3) 0.10659(10) 0.0394(8) Uani 1 1 d .
C23 C 0.7812(4) 0.4436(3) 0.07744(9) 0.0364(8) Uani 1 1 d .
H23 H 0.8038 0.5354 0.0648 0.044 Uiso 1 1 calc R
C24 C 0.8773(3) 0.3279(3) 0.06669(9) 0.0328(7) Uani 1 1 d .
H24 H 0.9623 0.3398 0.0456 0.039 Uiso 1 1 calc R
C25 C 0.4217(5) 0.5332(4) 0.14144(14) 0.0804(14) Uani 1 1 d .
H25A H 0.3512 0.4577 0.1295 0.121 Uiso 1 1 calc R
H25B H 0.3628 0.6247 0.1421 0.121 Uiso 1 1 calc R
H25C H 0.4556 0.5077 0.1720 0.121 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C22 O4 C25 117.2(2)
C1 N1 C13 118.5(2)
C1 N1 C9 125.3(2)
C13 N1 C9 114.3(2)
C14 N2 C10 109.0(2)
C18 N3 C14 113.4(2)
O3 N4 O2 124.4(3)
O3 N4 C6 118.2(3)
O2 N4 C6 117.4(3)
O1 C1 N1 120.9(3)
O1 C1 C2 121.8(3)
N1 C1 C2 117.2(3)
C1 C2 C3 112.0(2)
C2 C3 C4 109.8(2)
C2 C3 C8 108.9(2)
C4 C3 C8 112.8(2)
C5 C4 C3 111.4(2)
C6 C5 C4 107.6(2)
C5 C6 N4 109.1(2)
C5 C6 C7 112.3(2)
N4 C6 C7 108.9(2)
C19 C7 C6 109.7(2)
C19 C7 C8 116.5(2)
C6 C7 C8 108.1(2)
C3 C8 C7 108.9(2)
C3 C8 C9 108.9(2)
C7 C8 C9 112.1(2)
N1 C9 C10 103.8(2)
N1 C9 C8 113.8(2)
C10 C9 C8 117.8(2)
C11 C10 N2 109.0(2)
C11 C10 C9 125.9(2)
N2 C10 C9 124.8(2)
C10 C11 C15 106.8(2)
C10 C11 C12 123.2(3)
C15 C11 C12 129.6(3)
C11 C12 C13 107.0(2)
N1 C13 C12 109.9(2)
N3 C14 N2 124.7(3)
N3 C14 C15 127.0(3)
N2 C14 C15 108.3(2)
C16 C15 C14 117.3(3)
C16 C15 C11 135.9(3)
C14 C15 C11 106.8(2)
C17 C16 C15 116.9(3)
C16 C17 C18 120.3(3)
N3 C18 C17 125.0(3)
C20 C19 C24 117.2(3)
C20 C19 C7 120.1(3)
C24 C19 C7 122.7(3)
C21 C20 C19 121.9(3)
C20 C21 C22 120.0(3)
O4 C22 C21 125.2(3)
O4 C22 C23 115.6(3)
C21 C22 C23 119.2(3)
C24 C23 C22 120.5(3)
C23 C24 C19 121.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.241(3)
O2 N4 1.224(3)
O3 N4 1.215(3)
O4 C22 1.361(4)
O4 C25 1.427(4)
N1 C1 1.355(3)
N1 C13 1.470(3)
N1 C9 1.497(3)
N2 C14 1.368(3)
N2 C10 1.384(3)
N3 C18 1.336(4)
N3 C14 1.336(3)
N4 C6 1.517(4)
C1 C2 1.488(4)
C2 C3 1.513(4)
C3 C4 1.516(4)
C3 C8 1.541(4)
C4 C5 1.516(4)
C5 C6 1.515(4)
C6 C7 1.547(4)
C7 C19 1.508(4)
C7 C8 1.562(4)
C8 C9 1.564(3)
C9 C10 1.517(4)
C10 C11 1.382(4)
C11 C15 1.433(4)
C11 C12 1.491(4)
C12 C13 1.520(4)
C14 C15 1.406(4)
C15 C16 1.396(4)
C16 C17 1.382(4)
C17 C18 1.390(4)
C19 C20 1.390(4)
C19 C24 1.402(4)
C20 C21 1.380(4)
C21 C22 1.380(4)
C22 C23 1.388(4)
C23 C24 1.376(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5B O1 0.84(4) 2.25(4) 2.942(3) 140(4) 1_465
O5 H5A N3 0.80(4) 2.36(4) 2.907(3) 126(4) .
