#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/70/1517076.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_1517076
loop_
_publ_author_name
'Talukdar, Ranadeep'
'Tiwari, Deo Prakash'
'Saha, Amrita'
'Ghorai, Manas K.'
_publ_section_title
;
 Diastereoselective Synthesis of Functionalized Tetrahydrocarbazoles via a
 Domino-Ring Opening-Cyclization of Donor-Acceptor Cyclopropanes with
 Substituted 2-Vinylindoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3954
_journal_page_last               3957
_journal_paper_doi               10.1021/ol501763n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C25 H26 N2 O7'
_chemical_formula_weight         466.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 107.750(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.398(5)
_cell_length_b                   23.088(5)
_cell_length_c                   12.083(5)
_cell_measurement_reflns_used    3175
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.50
_cell_volume                     2231.3(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12723
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0383P)²+0.9264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2904
_reflns_number_total             4144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501763n_si_002.cif
_cod_data_source_block           3sepb_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517075--1517076.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1517076
loop_
_symmetry_equiv_pos_as_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_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
O3 O 0.62015(16) 0.33300(6) 1.11195(11) 0.0169(3) Uani 1 1 d .
C2 C -0.3612(2) 0.30264(9) 0.82426(17) 0.0176(5) Uani 1 1 d .
H2 H -0.3978 0.2646 0.8233 0.021 Uiso 1 1 calc R
C5 C -0.2496(3) 0.41857(9) 0.82461(17) 0.0190(5) Uani 1 1 d .
H5 H -0.2138 0.4566 0.8238 0.023 Uiso 1 1 calc R
C18 C 0.2359(3) 0.53145(9) 0.73966(17) 0.0178(5) Uani 1 1 d .
H18 H 0.2705 0.5697 0.7387 0.021 Uiso 1 1 calc R
O7 O 0.21573(18) 0.51627(6) 0.53567(11) 0.0206(3) Uani 1 1 d .
O6 O 0.31612(17) 0.42461(6) 1.24329(11) 0.0198(3) Uani 1 1 d .
O5 O 0.17092(17) 0.34291(6) 1.24167(12) 0.0207(4) Uani 1 1 d .
O1 O 0.52589(19) 0.19331(7) 0.98137(15) 0.0321(4) Uani 1 1 d .
O4 O 0.57066(17) 0.32683(6) 1.28370(12) 0.0198(3) Uani 1 1 d .
N1 N -0.06213(19) 0.28374(7) 0.94081(14) 0.0151(4) Uani 1 1 d .
O2 O 0.4818(2) 0.21475(7) 1.14377(14) 0.0319(4) Uani 1 1 d .
C17 C 0.2014(2) 0.49783(9) 0.64032(17) 0.0159(5) Uani 1 1 d .
C1 C -0.1952(2) 0.31768(9) 0.87872(16) 0.0148(5) Uani 1 1 d .
C9 C -0.0744(3) 0.22436(8) 0.97780(17) 0.0171(5) Uani 1 1 d .
H9A H -0.0137 0.1992 0.9418 0.026 Uiso 1 1 calc R
H9B H -0.1897 0.2129 0.9553 0.026 Uiso 1 1 calc R
H9C H -0.0279 0.2218 1.0607 0.026 Uiso 1 1 calc R
C11 C 0.3429(2) 0.35166(8) 1.11260(16) 0.0136(4) Uani 1 1 d .
C4 C -0.4150(3) 0.40405(10) 0.77244(18) 0.0217(5) Uani 1 1 d .
H4 H -0.4913 0.4328 0.7374 0.026 Uiso 1 1 calc R
C7 C 0.0388(2) 0.37446(9) 0.94091(16) 0.0145(4) Uani 1 1 d .
C8 C 0.0773(2) 0.31911(9) 0.97807(16) 0.0147(5) Uani 1 1 d .
C12 C 0.3396(2) 0.39994(9) 1.02337(16) 0.0146(5) Uani 1 1 d .
H12A H 0.4079 0.4320 1.0633 0.018 Uiso 1 1 calc R
H12B H 0.3895 0.3852 0.9664 0.018 Uiso 1 1 calc R
C10 C 0.2444(2) 0.29734(8) 1.05088(17) 0.0144(4) Uani 1 1 d .
H10 H 0.2278 0.2711 1.1102 0.017 Uiso 1 1 calc R
C24 C 0.2635(2) 0.37144(9) 1.20523(16) 0.0148(5) Uani 1 1 d .
N2 N 0.4546(2) 0.22062(8) 1.03891(16) 0.0218(4) Uani 1 1 d .
C19 C 0.2182(2) 0.50749(9) 0.84165(17) 0.0178(5) Uani 1 1 d .
H19 H 0.2415 0.5302 0.9083 0.021 Uiso 1 1 calc R
C15 C 0.1324(2) 0.41816(9) 0.74407(17) 0.0163(5) Uani 1 1 d .
H15 H 0.0976 0.3800 0.7447 0.020 Uiso 1 1 calc R
C14 C 0.1669(2) 0.45093(9) 0.84567(16) 0.0139(4) Uani 1 1 d .
C21 C 0.3253(2) 0.26365(9) 0.97425(17) 0.0171(5) Uani 1 1 d .
H21A H 0.2388 0.2432 0.9154 0.020 Uiso 1 1 calc R
H21B H 0.3774 0.2908 0.9347 0.020 Uiso 1 1 calc R
C16 C 0.1489(2) 0.44109(9) 0.64291(17) 0.0168(5) Uani 1 1 d .
H16 H 0.1247 0.4184 0.5762 0.020 Uiso 1 1 calc R
C13 C 0.1627(2) 0.42282(9) 0.95919(16) 0.0149(4) Uani 1 1 d .
H13 H 0.1332 0.4525 1.0076 0.018 Uiso 1 1 calc R
C6 C -0.1368(2) 0.37503(9) 0.87866(16) 0.0149(4) Uani 1 1 d .
C3 C -0.4693(3) 0.34670(9) 0.77155(17) 0.0196(5) Uani 1 1 d .
H3 H -0.5811 0.3380 0.7346 0.024 Uiso 1 1 calc R
C22 C 0.5224(2) 0.33563(8) 1.18011(18) 0.0153(5) Uani 1 1 d .
C23 C 0.7934(2) 0.31687(10) 1.16889(18) 0.0238(5) Uani 1 1 d .
H23A H 0.8365 0.3391 1.2388 0.036 Uiso 1 1 calc R
H23B H 0.8587 0.3245 1.1176 0.036 Uiso 1 1 calc R
H23C H 0.7993 0.2764 1.1879 0.036 Uiso 1 1 calc R
C25 C 0.2609(3) 0.44583(10) 1.33877(18) 0.0256(5) Uani 1 1 d .
H25A H 0.1426 0.4528 1.3117 0.038 Uiso 1 1 calc R
H25B H 0.3182 0.4813 1.3680 0.038 Uiso 1 1 calc R
H25C H 0.2854 0.4175 1.3997 0.038 Uiso 1 1 calc R
C20 C 0.2631(3) 0.57497(9) 0.52788(18) 0.0232(5) Uani 1 1 d .
H20A H 0.1858 0.6001 0.5488 0.035 Uiso 1 1 calc R
H20B H 0.2617 0.5832 0.4497 0.035 Uiso 1 1 calc R
H20C H 0.3736 0.5812 0.5799 0.035 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 O3 C23 115.84(16)
C3 C2 C1 117.17(19)
C4 C5 C6 118.8(2)
C17 C18 C19 119.5(2)
C17 O7 C20 117.42(16)
C24 O6 C25 115.48(16)
C1 N1 C8 107.76(16)
C1 N1 C9 125.38(17)
C8 N1 C9 125.98(16)
O7 C17 C18 124.80(19)
O7 C17 C16 115.56(17)
C18 C17 C16 119.63(19)
N1 C1 C2 129.93(19)
N1 C1 C6 107.94(17)
C2 C1 C6 122.12(19)
C22 C11 C24 105.09(16)
C22 C11 C12 110.67(16)
C24 C11 C12 111.99(16)
C22 C11 C10 110.73(16)
C24 C11 C10 107.59(16)
C12 C11 C10 110.61(15)
C5 C4 C3 120.9(2)
C8 C7 C6 106.50(17)
C8 C7 C13 124.61(18)
C6 C7 C13 128.84(18)
C7 C8 N1 110.76(17)
C7 C8 C10 126.49(18)
N1 C8 C10 122.74(18)
C13 C12 C11 114.02(16)
C8 C10 C21 109.08(16)
C8 C10 C11 106.03(16)
C21 C10 C11 115.61(16)
O5 C24 O6 124.08(19)
O5 C24 C11 125.28(18)
O6 C24 C11 110.60(17)
O1 N2 O2 124.24(18)
O1 N2 C21 116.54(18)
O2 N2 C21 119.22(17)
C14 C19 C18 121.53(19)
C16 C15 C14 121.5(2)
C19 C14 C15 117.73(19)
C19 C14 C13 121.76(18)
C15 C14 C13 120.28(18)
N2 C21 C10 114.08(17)
C15 C16 C17 120.16(19)
C7 C13 C14 112.94(16)
C7 C13 C12 109.77(16)
C14 C13 C12 108.33(16)
C5 C6 C1 119.22(18)
C5 C6 C7 133.78(19)
C1 C6 C7 107.00(17)
C2 C3 C4 121.70(19)
O4 C22 O3 123.91(19)
O4 C22 C11 124.00(18)
O3 C22 C11 112.08(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C22 1.330(2)
O3 C23 1.456(2)
C2 C3 1.383(3)
C2 C1 1.392(3)
C5 C4 1.380(3)
C5 C6 1.399(3)
C18 C17 1.384(3)
C18 C19 1.400(3)
O7 C17 1.374(2)
O7 C20 1.424(2)
O6 C24 1.338(2)
O6 C25 1.453(2)
O5 C24 1.200(2)
O1 N2 1.222(2)
O4 C22 1.209(2)
N1 C1 1.384(2)
N1 C8 1.385(3)
N1 C9 1.455(2)
O2 N2 1.225(2)
C17 C16 1.386(3)
C1 C6 1.412(3)
C11 C22 1.525(3)
C11 C24 1.537(3)
C11 C12 1.545(3)
C11 C10 1.561(3)
C4 C3 1.400(3)
C7 C8 1.360(3)
C7 C6 1.437(3)
C7 C13 1.496(3)
C8 C10 1.498(3)
C12 C13 1.544(3)
C10 C21 1.519(3)
N2 C21 1.503(3)
C19 C14 1.381(3)
C15 C16 1.377(3)
C15 C14 1.395(3)
C14 C13 1.527(3)
