#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/15/7151559.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_7151559
loop_
_publ_author_name
'Ley, Steven V.'
'Cleator, Ed'
'Hewitt, Peter R.'
_publ_section_title
;
 A rapid stereocontrolled synthesis of the
 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for
 10b-hydroxy-pyrazino[1?,2?:1,5]pyrrolo[2,3-b]indole-1,4-diones
;
_journal_issue                   20
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              3492
_journal_paper_doi               10.1039/b308288a
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C17 H22 N2 O5,C H Cl3'
_chemical_formula_sum            'C18 H23 Cl3 N2 O5'
_chemical_formula_weight         453.73
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.081(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2184(6)
_cell_length_b                   6.3844(3)
_cell_length_c                   14.8429(9)
_cell_measurement_reflns_used    5923
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     1100.68(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5544
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1046P)²+0.5374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                2908
_reflns_number_total             3372
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b308288a.txt
_cod_data_source_block           sl0251
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7151559
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7119(3) -0.1063(7) 0.7178(2) 0.0524(9) Uani 1 1 d . . .
O2 O 0.5540(2) -0.1772(5) 0.76121(19) 0.0360(7) Uani 1 1 d . . .
O3 O 0.5843(2) 0.4478(4) 0.95152(19) 0.0256(6) Uani 1 1 d . . .
H3 H 0.530(4) 0.423(8) 0.985(3) 0.031 Uiso 1 1 d . . .
O4 O 0.6590(3) -0.3128(6) 1.1472(2) 0.0472(9) Uani 1 1 d . . .
O5 O 0.8155(3) -0.1253(6) 1.2162(2) 0.0473(9) Uani 1 1 d . . .
N1 N 0.6856(3) 0.0408(5) 0.8491(2) 0.0268(7) Uani 1 1 d . . .
N2 N 0.6145(3) -0.0864(5) 0.9790(2) 0.0224(7) Uani 1 1 d . . .
H2 H 0.614(4) -0.199(9) 0.960(3) 0.027 Uiso 1 1 d . . .
C1 C 0.3852(6) -0.3619(13) 0.6941(4) 0.078(2) Uani 1 1 d . . .
H1A H 0.3445 -0.2317 0.6981 0.117 Uiso 1 1 calc R . .
H1B H 0.3991 -0.4410 0.7532 0.117 Uiso 1 1 calc R . .
H1C H 0.3382 -0.4462 0.6409 0.117 Uiso 1 1 calc R . .
C2 C 0.5720(6) -0.5085(10) 0.6834(4) 0.0673(16) Uani 1 1 d . . .
H2B H 0.6429 -0.4727 0.6692 0.101 Uiso 1 1 calc R . .
H2C H 0.5279 -0.6105 0.6369 0.101 Uiso 1 1 calc R . .
H2D H 0.5915 -0.5690 0.7471 0.101 Uiso 1 1 calc R . .
C3 C 0.4997(4) -0.3105(8) 0.6787(3) 0.0404(11) Uani 1 1 d . . .
C4 C 0.4806(5) -0.1886(10) 0.5875(3) 0.0593(15) Uani 1 1 d . . .
H4A H 0.4423 -0.0558 0.5916 0.089 Uiso 1 1 calc R . .
H4B H 0.4323 -0.2708 0.5342 0.089 Uiso 1 1 calc R . .
H4C H 0.5550 -0.1605 0.5778 0.089 Uiso 1 1 calc R . .
C5 C 0.6544(3) -0.0847(7) 0.7703(3) 0.0332(9) Uani 1 1 d . . .
C6 C 0.7746(3) 0.1906(7) 0.8691(3) 0.0281(8) Uani 1 1 d . . .
C7 C 0.8638(4) 0.2150(8) 0.8302(3) 0.0391(10) Uani 1 1 d . . .
H7 H 0.8728 0.1197 0.7839 0.047 Uiso 1 1 calc R . .
C8 C 0.9391(4) 0.3805(9) 0.8604(3) 0.0455(12) Uani 1 1 d . . .
H8 H 0.9995 0.3998 0.8335 0.055 Uiso 1 1 calc R . .
C9 C 0.9286(4) 0.5185(8) 0.9289(4) 0.0430(11) Uani 1 1 d . . .
H9 H 0.9812 0.6316 0.9482 0.052 Uiso 1 1 calc R . .
C10 C 0.8408(3) 0.4924(7) 0.9697(3) 0.0353(10) Uani 1 1 d . . .
H10 H 0.8342 0.5848 1.0180 0.042 Uiso 1 1 calc R . .
C11 C 0.7638(3) 0.3295(6) 0.9386(3) 0.0256(8) Uani 1 1 d . . .
C12 C 0.6598(3) 0.2751(6) 0.9694(3) 0.0237(8) Uani 1 1 d . . .
C13 C 0.6960(3) 0.1966(6) 1.0726(3) 0.0259(8) Uani 1 1 d . . .
H13A H 0.7675 0.2657 1.1117 0.031 Uiso 1 1 calc R . .
H13B H 0.6344 0.2198 1.1019 0.031 Uiso 1 1 calc R . .
C14 C 0.7152(3) -0.0378(6) 1.0601(3) 0.0249(8) Uani 1 1 d . . .
H14 H 0.7864 -0.0562 1.0413 0.030 Uiso 1 1 calc R . .
C15 C 0.6091(3) 0.0767(6) 0.9097(2) 0.0220(8) Uani 1 1 d . . .
H15 H 0.5278 0.1017 0.8695 0.026 Uiso 1 1 calc R . .
C16 C 0.7231(3) -0.1737(6) 1.1440(3) 0.0281(9) Uani 1 1 d . . .
C17 C 0.8355(5) -0.2537(11) 1.3012(4) 0.0583(14) Uani 1 1 d . . .
H17A H 0.8994 -0.1947 1.3524 0.087 Uiso 1 1 calc R . .
H17B H 0.8547 -0.3969 1.2878 0.087 Uiso 1 1 calc R . .
H17C H 0.7658 -0.2556 1.3206 0.087 Uiso 1 1 calc R . .
C18 C 0.8709(4) -0.2182(9) 0.6055(4) 0.0501(13) Uani 1 1 d . . .
H18 H 0.8232 -0.1997 0.6488 0.060 Uiso 1 1 calc R . .
Cl1 Cl 0.8104(2) -0.4205(4) 0.52797(15) 0.1123(9) Uani 1 1 d . . .
Cl2 Cl 1.01086(17) -0.2747(4) 0.67552(18) 0.1063(8) Uani 1 1 d . . .
Cl3 Cl 0.8683(2) 0.0138(4) 0.54692(16) 0.1200(9) Uani 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C5 O2 C3 120.3(3) . . ?
C16 O5 C17 116.0(4) . . ?
C5 N1 C6 124.7(3) . . ?
C5 N1 C15 122.7(3) . . ?
C6 N1 C15 110.7(3) . . ?
C15 N2 C14 105.8(3) . . ?
O2 C3 C4 110.6(4) . . ?
O2 C3 C1 101.4(4) . . ?
C4 C3 C1 110.5(5) . . ?
O2 C3 C2 109.6(4) . . ?
C4 C3 C2 113.0(4) . . ?
C1 C3 C2 111.0(5) . . ?
O1 C5 O2 126.0(4) . . ?
O1 C5 N1 123.6(4) . . ?
O2 C5 N1 110.4(3) . . ?
C7 C6 C11 120.0(4) . . ?
C7 C6 N1 129.9(4) . . ?
C11 C6 N1 110.0(3) . . ?
C8 C7 C6 118.7(4) . . ?
C9 C8 C7 121.5(4) . . ?
C8 C9 C10 120.2(4) . . ?
C11 C10 C9 118.7(4) . . ?
C10 C11 C6 120.9(3) . . ?
C10 C11 C12 128.2(4) . . ?
C6 C11 C12 110.9(3) . . ?
O3 C12 C11 108.9(3) . . ?
O3 C12 C13 114.3(3) . . ?
C11 C12 C13 111.4(3) . . ?
O3 C12 C15 114.0(3) . . ?
C11 C12 C15 103.7(3) . . ?
C13 C12 C15 104.0(3) . . ?
C14 C13 C12 101.8(3) . . ?
N2 C14 C16 112.5(3) . . ?
N2 C14 C13 100.7(3) . . ?
C16 C14 C13 115.9(3) . . ?
N2 C15 N1 114.5(3) . . ?
N2 C15 C12 104.9(3) . . ?
N1 C15 C12 104.7(3) . . ?
O4 C16 O5 123.0(4) . . ?
O4 C16 C14 126.2(4) . . ?
O5 C16 C14 110.8(3) . . ?
Cl3 C18 Cl1 111.7(3) . . ?
Cl3 C18 Cl2 110.0(3) . . ?
Cl1 C18 Cl2 112.3(3) . . ?
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
O1 C5 1.207(5) . ?
O2 C5 1.330(5) . ?
O2 C3 1.469(5) . ?
O3 C12 1.409(5) . ?
O4 C16 1.195(5) . ?
O5 C16 1.329(5) . ?
O5 C17 1.461(6) . ?
N1 C5 1.371(5) . ?
N1 C6 1.409(5) . ?
N1 C15 1.502(4) . ?
N2 C15 1.451(5) . ?
N2 C14 1.464(5) . ?
C1 C3 1.522(7) . ?
C2 C3 1.531(8) . ?
C3 C4 1.515(7) . ?
C6 C7 1.391(5) . ?
C6 C11 1.399(6) . ?
C7 C8 1.381(7) . ?
C8 C9 1.380(7) . ?
C9 C10 1.396(6) . ?
C10 C11 1.383(6) . ?
C11 C12 1.517(5) . ?
C12 C13 1.541(5) . ?
C12 C15 1.560(5) . ?
C13 C14 1.535(6) . ?
C14 C16 1.497(6) . ?
C18 Cl3 1.713(6) . ?
C18 Cl1 1.734(6) . ?
C18 Cl2 1.741(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189025
