#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:02:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180220 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/06/7110610.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110610
loop_
_publ_author_name
'Hsieh, Ming-Fang'
'Rao, Polisetti Dharma'
'Liao, Chun-Chen'
_publ_section_title
;
 Diels--Alder and Michael addition reactions of indoles with masked
 o-benzoquinones: synthesis of highly functionalized hydrocarbazoles and
 3-arylindoles
;
_journal_issue                   15
_journal_name_full               'Chemical Communications'
_journal_page_first              1441
_journal_paper_doi               10.1039/a904366g
_journal_year                    1999
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.726(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6487(14)
_cell_length_b                   22.172(3)
_cell_length_c                   8.588(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.6
_cell_measurement_theta_min      9.35
_cell_volume                     2017.5(6)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'NRCSDP DATARD2'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3545
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   psi
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0049(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.068
_refine_ls_goodness_of_fit_obs   1.225
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_restrained_S_obs      1.225
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_obs          0.0430
_refine_ls_shift/esd_max         0.013
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0767P)²+0.0989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1403
_refine_ls_wR_factor_obs         0.1261
_reflns_number_observed          2267
_reflns_number_total             3545
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904366gsup1.cif
_cod_data_source_block           ic6143
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.0989P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.0989P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2017.5(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7110610
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2108(2) 0.71537(7) 0.9304(2) 0.0538(5) Uani 1 d .
O2 O 0.3574(2) 0.50082(8) 1.2868(2) 0.0628(5) Uani 1 d .
O3 O 0.32782(14) 0.60171(7) 0.9203(2) 0.0431(4) Uani 1 d .
O4 O 0.11783(14) 0.59162(7) 0.8179(2) 0.0393(4) Uani 1 d .
O5 O -0.2620(2) 0.59533(8) 1.0027(2) 0.0641(5) Uani 1 d .
O6 O -0.29800(15) 0.68669(8) 0.8969(2) 0.0574(5) Uani 1 d .
N1 N -0.0078(2) 0.53740(8) 1.2401(2) 0.0362(4) Uani 1 d .
H1A H 0.0108(2) 0.50029(8) 1.2604(2) 0.043 Uiso 1 calc R
C1 C 0.2430(2) 0.58955(10) 1.2315(2) 0.0367(5) Uani 1 d .
C2 C 0.2128(2) 0.64542(10) 1.2674(2) 0.0377(5) Uani 1 d .
H2A H 0.2487(2) 0.66486(10) 1.3570(2) 0.045 Uiso 1 calc R
C3 C 0.1163(2) 0.67510(9) 1.1527(2) 0.0357(5) Uani 1 d .
H3A H 0.1007(2) 0.71694(9) 1.1821(2) 0.043 Uiso 1 calc R
C4 C 0.1802(2) 0.67169(9) 1.0015(3) 0.0363(5) Uani 1 d .
C5 C 0.2026(2) 0.60590(9) 0.9511(2) 0.0337(5) Uani 1 d .
C6 C 0.1686(2) 0.56508(9) 1.0860(2) 0.0311(5) Uani 1 d .
H6A H 0.1915(2) 0.52306(9) 1.0677(2) 0.037 Uiso 1 calc R
C7 C 0.0265(2) 0.57071(8) 1.1032(2) 0.0307(5) Uani 1 d .
H7A H -0.0225(2) 0.55573(8) 1.0084(2) 0.037 Uiso 1 calc R
C8 C -0.0083(2) 0.63772(9) 1.1322(2) 0.0318(5) Uani 1 d .
C9 C -0.0739(2) 0.63414(9) 1.2809(2) 0.0344(5) Uani 1 d .
C10 C -0.1351(2) 0.67822(10) 1.3554(3) 0.0453(6) Uani 1 d .
H10A H -0.1362(2) 0.71774(10) 1.3189(3) 0.054 Uiso 1 calc R
C11 C -0.1958(2) 0.66309(11) 1.4866(3) 0.0549(7) Uani 1 d .
H11A H -0.2359(2) 0.69279(11) 1.5400(3) 0.066 Uiso 1 calc R
C12 C -0.1964(2) 0.60415(12) 1.5370(3) 0.0524(7) Uani 1 d .
H12A H -0.2379(2) 0.59443(12) 1.6239(3) 0.063 Uiso 1 calc R
C13 C -0.1363(2) 0.55901(11) 1.4609(3) 0.0436(6) Uani 1 d .
H13A H -0.1374(2) 0.51929(11) 1.4956(3) 0.052 Uiso 1 calc R
C14 C -0.0745(2) 0.57447(9) 1.3319(2) 0.0338(5) Uani 1 d .
C15 C 0.3452(2) 0.55359(11) 1.3170(3) 0.0434(6) Uani 1 d .
C16 C 0.4360(3) 0.58444(15) 1.4365(4) 0.0809(10) Uani 1 d .
H16A H 0.4963(3) 0.55566(15) 1.4818(4) 0.121 Uiso 1 calc R
H16B H 0.3904(3) 0.60136(15) 1.5170(4) 0.121 Uiso 1 calc R
H16C H 0.4792(3) 0.61601(15) 1.3870(4) 0.121 Uiso 1 calc R
C17 C 0.3679(2) 0.54255(11) 0.8769(3) 0.0587(7) Uani 1 d .
H17A H 0.4552(2) 0.54385(11) 0.8579(3) 0.088 Uiso 1 calc R
H17B H 0.3179(2) 0.52965(11) 0.7836(3) 0.088 Uiso 1 calc R
H17C H 0.3573(2) 0.51469(11) 0.9601(3) 0.088 Uiso 1 calc R
C18 C 0.1378(3) 0.62396(12) 0.6765(3) 0.0564(7) Uani 1 d .
H18A H 0.0764(3) 0.61137(12) 0.5935(3) 0.085 Uiso 1 calc R
H18B H 0.2210(3) 0.61552(12) 0.6482(3) 0.085 Uiso 1 calc R
H18C H 0.1294(3) 0.66648(12) 0.6938(3) 0.085 Uiso 1 calc R
C19 C -0.0929(2) 0.66712(9) 0.9988(3) 0.0379(5) Uani 1 d .
H19A H -0.0965(2) 0.71004(9) 1.0197(3) 0.045 Uiso 1 calc R
H19B H -0.0528(2) 0.66216(9) 0.9030(3) 0.045 Uiso 1 calc R
C20 C -0.2251(2) 0.64404(10) 0.9705(3) 0.0397(5) Uani 1 d .
C21 C -0.4291(2) 0.67169(14) 0.8546(4) 0.0715(9) Uani 1 d .
H21A H -0.4710(2) 0.66351(14) 0.9476(4) 0.086 Uiso 1 calc R
H21B H -0.4359(2) 0.63619(14) 0.7883(4) 0.086 Uiso 1 calc R
C22 C -0.4879(3) 0.7244(2) 0.7694(5) 0.0991(13) Uani 1 d .
H22A H -0.5754(3) 0.7162(2) 0.7391(5) 0.149 Uiso 1 calc R
H22B H -0.4456(3) 0.7320(2) 0.6778(5) 0.149 Uiso 1 calc R
H22C H -0.4806(3) 0.7592(2) 0.8363(5) 0.149 Uiso 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
C5 O3 C17 115.2(2)
C5 O4 C18 115.5(2)
C20 O6 C21 117.1(2)
C14 N1 C7 109.9(2)
C2 C1 C15 124.8(2)
C2 C1 C6 114.1(2)
C15 C1 C6 121.0(2)
C1 C2 C3 115.0(2)
C2 C3 C4 101.7(2)
C2 C3 C8 111.1(2)
C4 C3 C8 108.9(2)
O1 C4 C3 123.8(2)
O1 C4 C5 123.9(2)
C3 C4 C5 112.3(2)
O3 C5 O4 112.2(2)
O3 C5 C6 113.9(2)
O4 C5 C6 107.2(2)
O3 C5 C4 107.1(2)
O4 C5 C4 109.4(2)
C6 C5 C4 106.8(2)
C1 C6 C7 109.3(2)
C1 C6 C5 105.5(2)
C7 C6 C5 109.3(2)
N1 C7 C6 111.2(2)
N1 C7 C8 105.6(2)
C6 C7 C8 110.2(2)
C9 C8 C19 111.5(2)
C9 C8 C7 102.8(2)
C19 C8 C7 114.7(2)
C9 C8 C3 113.0(2)
C19 C8 C3 106.7(2)
C7 C8 C3 108.1(2)
C10 C9 C14 121.0(2)
C10 C9 C8 129.5(2)
C14 C9 C8 109.3(2)
C9 C10 C11 119.1(2)
C12 C11 C10 119.9(2)
C11 C12 C13 121.4(2)
C14 C13 C12 118.4(2)
N1 C14 C13 128.3(2)
N1 C14 C9 111.5(2)
C13 C14 C9 120.2(2)
O2 C15 C1 120.2(2)
O2 C15 C16 120.8(2)
C1 C15 C16 118.9(2)
C20 C19 C8 116.7(2)
O5 C20 O6 124.0(2)
O5 C20 C19 126.9(2)
O6 C20 C19 109.1(2)
O6 C21 C22 107.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.207(2)
O2 C15 1.208(3)
O3 C5 1.388(3)
O3 C17 1.440(3)
O4 C5 1.420(2)
O4 C18 1.445(3)
O5 C20 1.191(3)
O6 C20 1.341(3)
O6 C21 1.446(3)
N1 C14 1.383(3)
N1 C7 1.466(3)
C1 C2 1.324(3)
C1 C15 1.483(3)
C1 C6 1.512(3)
C2 C3 1.503(3)
C3 C4 1.526(3)
C3 C8 1.560(3)
C4 C5 1.547(3)
C5 C6 1.542(3)
C6 C7 1.540(3)
C7 C8 1.557(3)
C8 C9 1.518(3)
C8 C19 1.531(3)
C9 C10 1.368(3)
C9 C14 1.394(3)
C10 C11 1.395(3)
C11 C12 1.377(4)
C12 C13 1.386(3)
C13 C14 1.388(3)
C15 C16 1.502(4)
C19 C20 1.495(3)
C21 C22 1.484(4)
