#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:47:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180518 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/87/7218722.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_7218722
loop_
_publ_author_name
'Yan, Chao Guo'
'Zhu, Dan'
'Sun, Jing'
_publ_section_title
;
 One-pot synthesis of 6,11-dihydro-5H-indolizino[8,7-b]indoles via
 sequential formation of β-enamino ester, Michael addition and
 Pictet-Spengler reactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10355F
_journal_year                    2014
_chemical_formula_moiety         'C28 H23 Cl N2 O4'
_chemical_formula_sum            'C28 H23 Cl N2 O4'
_chemical_formula_weight         486.93
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.047(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0614(17)
_cell_length_b                   9.0234(13)
_cell_length_c                   22.676(3)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.43
_cell_volume                     2467.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21008
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016.0
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0591P)²+0.6776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                3789
_reflns_number_total             5652
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10355f2.cif
_cod_data_source_block           4b
_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/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7218722
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.68592(18) 0.4550(2) 0.51715(10) 0.0558(5) Uani 1 1 d .
H1 H 0.7335 0.4089 0.4911 0.067 Uiso 1 1 calc R
C2 C 0.65121(19) 0.3799(3) 0.56751(11) 0.0637(6) Uani 1 1 d .
C3 C 0.6881(2) 0.2224(3) 0.57926(13) 0.0890(9) Uani 1 1 d .
H3A H 0.7372 0.2204 0.6131 0.134 Uiso 1 1 calc R
H3B H 0.7260 0.1849 0.5455 0.134 Uiso 1 1 calc R
H3C H 0.6245 0.1617 0.5867 0.134 Uiso 1 1 calc R
C4 C 0.5810(2) 0.4530(3) 0.60538(10) 0.0673(7) Uani 1 1 d .
H4 H 0.5585 0.4040 0.6392 0.081 Uiso 1 1 calc R
C5 C 0.54241(18) 0.5967(3) 0.59531(9) 0.0612(6) Uani 1 1 d .
H5 H 0.4948 0.6432 0.6213 0.073 Uiso 1 1 calc R
C6 C 0.57830(16) 0.6671(2) 0.54470(8) 0.0485(5) Uani 1 1 d .
C7 C 0.60941(15) 0.8411(2) 0.47330(8) 0.0434(4) Uani 1 1 d .
C8 C 0.67055(14) 0.7001(2) 0.45508(7) 0.0418(4) Uani 1 1 d .
H8 H 0.6282 0.6594 0.4215 0.050 Uiso 1 1 calc R
C9 C 0.64957(15) 0.5972(2) 0.50622(8) 0.0454(4) Uani 1 1 d .
C10 C 0.78801(15) 0.7116(2) 0.43521(7) 0.0418(4) Uani 1 1 d .
C11 C 0.88650(16) 0.7313(2) 0.47031(8) 0.0513(5) Uani 1 1 d .
C12 C 0.89844(18) 0.7659(3) 0.53318(9) 0.0595(5) Uani 1 1 d .
C13 C 0.8064(2) 0.8583(3) 0.61669(9) 0.0761(7) Uani 1 1 d .
H13A H 0.8248 0.7702 0.6385 0.114 Uiso 1 1 calc R
H13B H 0.7339 0.8917 0.6274 0.114 Uiso 1 1 calc R
H13C H 0.8598 0.9342 0.6256 0.114 Uiso 1 1 calc R
C14 C 0.97458(17) 0.7101(3) 0.43413(9) 0.0605(6) Uani 1 1 d .
H14 H 1.0488 0.7153 0.4457 0.073 Uiso 1 1 calc R
C15 C 0.82111(15) 0.6798(2) 0.37869(8) 0.0425(4) Uani 1 1 d .
C16 C 0.75071(14) 0.6432(2) 0.32688(7) 0.0409(4) Uani 1 1 d .
C17 C 0.66945(16) 0.7423(2) 0.30822(8) 0.0483(4) Uani 1 1 d .
H17 H 0.6624 0.8326 0.3276 0.058 Uiso 1 1 calc R
C18 C 0.59885(17) 0.7094(2) 0.26148(9) 0.0518(5) Uani 1 1 d .
H18 H 0.5449 0.7771 0.2494 0.062 Uiso 1 1 calc R
C19 C 0.60880(16) 0.5760(2) 0.23292(8) 0.0468(4) Uani 1 1 d .
C20 C 0.68821(19) 0.4761(2) 0.25030(10) 0.0615(6) Uani 1 1 d .
H20 H 0.6945 0.3860 0.2308 0.074 Uiso 1 1 calc R
C21 C 0.75910(18) 0.5097(2) 0.29706(9) 0.0562(5) Uani 1 1 d .
H21 H 0.8132 0.4417 0.3086 0.067 Uiso 1 1 calc R
C22 C 1.00694(15) 0.6564(2) 0.32887(8) 0.0470(4) Uani 1 1 d .
C23 C 0.98367(16) 0.7210(2) 0.27513(9) 0.0513(5) Uani 1 1 d .
H23 H 0.9222 0.7825 0.2708 0.062 Uiso 1 1 calc R
C24 C 1.05141(16) 0.6951(2) 0.22699(9) 0.0505(5) Uani 1 1 d .
H24 H 1.0335 0.7353 0.1903 0.061 Uiso 1 1 calc R
C25 C 1.14548(16) 0.6090(2) 0.23448(9) 0.0521(5) Uani 1 1 d .
C26 C 1.1879(2) 0.6132(3) 0.13188(10) 0.0865(8) Uani 1 1 d .
H26A H 1.1176 0.5684 0.1226 0.130 Uiso 1 1 calc R
H26B H 1.2430 0.5755 0.1058 0.130 Uiso 1 1 calc R
H26C H 1.1822 0.7187 0.1273 0.130 Uiso 1 1 calc R
C27 C 1.17012(17) 0.5483(2) 0.28892(9) 0.0583(5) Uani 1 1 d .
H27 H 1.2345 0.4926 0.2941 0.070 Uiso 1 1 calc R
C28 C 1.10060(16) 0.5690(2) 0.33588(9) 0.0547(5) Uani 1 1 d .
H28 H 1.1166 0.5245 0.3720 0.066 Uiso 1 1 calc R
Cl1 Cl 0.51889(5) 0.53542(7) 0.17410(2) 0.06662(19) Uani 1 1 d .
N1 N 0.55436(13) 0.81059(18) 0.52376(7) 0.0487(4) Uani 1 1 d .
H1A H 0.5104 0.8715 0.5407 0.058 Uiso 1 1 calc R
N2 N 0.93665(12) 0.68025(19) 0.37855(7) 0.0509(4) Uani 1 1 d .
O1 O 0.60509(11) 0.95801(15) 0.44586(6) 0.0545(4) Uani 1 1 d .
O2 O 0.97990(15) 0.7425(3) 0.56326(8) 0.1059(8) Uani 1 1 d .
O3 O 0.80708(12) 0.82640(17) 0.55454(6) 0.0593(4) Uani 1 1 d .
O4 O 1.21874(13) 0.5796(2) 0.19075(7) 0.0785(5) 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
C9 C1 C2 119.9(2)
C9 C1 H1 120.0
C2 C1 H1 120.0
C4 C2 C1 118.1(2)
C4 C2 C3 121.3(2)
C1 C2 C3 120.5(2)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C2 C4 C5 123.2(2)
C2 C4 H4 118.4
C5 C4 H4 118.4
C6 C5 C4 116.9(2)
C6 C5 H5 121.6
C4 C5 H5 121.6
C9 C6 C5 121.2(2)
C9 C6 N1 109.35(16)
C5 C6 N1 129.4(2)
O1 C7 N1 125.72(17)
O1 C7 C8 126.49(16)
N1 C7 C8 107.67(15)
C10 C8 C9 116.51(15)
C10 C8 C7 119.08(15)
C9 C8 C7 102.42(14)
C10 C8 H8 105.9
C9 C8 H8 105.9
C7 C8 H8 105.9
C1 C9 C6 120.59(18)
C1 C9 C8 130.81(18)
C6 C9 C8 108.56(16)
C15 C10 C11 106.95(16)
C15 C10 C8 123.80(16)
C11 C10 C8 128.48(16)
C14 C11 C10 107.19(17)
C14 C11 C12 123.39(18)
C10 C11 C12 129.42(18)
O2 C12 O3 122.6(2)
O2 C12 C11 125.4(2)
O3 C12 C11 112.02(17)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N2 C14 C11 109.38(18)
N2 C14 H14 125.3
C11 C14 H14 125.3
C10 C15 N2 107.94(15)
C10 C15 C16 127.93(16)
N2 C15 C16 124.06(15)
C21 C16 C17 117.97(17)
C21 C16 C15 122.51(17)
C17 C16 C15 119.47(16)
C18 C17 C16 121.22(18)
C18 C17 H17 119.4
C16 C17 H17 119.4
C19 C18 C17 119.53(18)
C19 C18 H18 120.2
C17 C18 H18 120.2
C20 C19 C18 120.56(18)
C20 C19 Cl1 120.31(15)
C18 C19 Cl1 119.13(16)
C19 C20 C21 119.74(19)
C19 C20 H20 120.1
C21 C20 H20 120.1
C20 C21 C16 120.98(19)
C20 C21 H21 119.5
C16 C21 H21 119.5
C23 C22 C28 119.74(18)
C23 C22 N2 121.13(17)
C28 C22 N2 119.12(18)
C22 C23 C24 120.63(18)
C22 C23 H23 119.7
C24 C23 H23 119.7
C25 C24 C23 119.26(19)
C25 C24 H24 120.4
C23 C24 H24 120.4
O4 C25 C27 116.20(18)
O4 C25 C24 124.04(19)
C27 C25 C24 119.76(18)
O4 C26 H26A 109.5
O4 C26 H26B 109.5
H26A C26 H26B 109.5
O4 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
C25 C27 C28 120.88(19)
C25 C27 H27 119.6
C28 C27 H27 119.6
C27 C28 C22 119.64(19)
C27 C28 H28 120.2
C22 C28 H28 120.2
C7 N1 C6 111.68(16)
C7 N1 H1A 124.2
C6 N1 H1A 124.2
C14 N2 C15 108.54(16)
C14 N2 C22 124.22(16)
C15 N2 C22 127.23(15)
C12 O3 C13 117.33(17)
C25 O4 C26 118.80(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.378(3)
C1 C2 1.398(3)
C1 H1 0.9300
C2 C4 1.384(3)
C2 C3 1.512(3)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 C5 1.395(3)
C4 H4 0.9300
C5 C6 1.388(3)
C5 H5 0.9300
C6 C9 1.388(3)
C6 N1 1.407(3)
C7 O1 1.226(2)
C7 N1 1.361(2)
C7 C8 1.531(3)
C8 C10 1.498(2)
C8 C9 1.510(2)
C8 H8 0.9800
C10 C15 1.379(2)
C10 C11 1.429(3)
C11 C14 1.368(3)
C11 C12 1.464(3)
C12 O2 1.205(2)
C12 O3 1.329(2)
C13 O3 1.439(2)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 N2 1.360(2)
C14 H14 0.9300
C15 N2 1.394(2)
C15 C16 1.475(2)
C16 C21 1.386(3)
C16 C17 1.387(3)
C17 C18 1.380(3)
C17 H17 0.9300
C18 C19 1.373(3)
C18 H18 0.9300
C19 C20 1.368(3)
C19 Cl1 1.7425(19)
C20 C21 1.383(3)
C20 H20 0.9300
C21 H21 0.9300
C22 C23 1.375(3)
C22 C28 1.385(3)
C22 N2 1.438(2)
C23 C24 1.395(3)
C23 H23 0.9300
C24 C25 1.383(3)
C24 H24 0.9300
C25 O4 1.366(2)
C25 C27 1.378(3)
C26 O4 1.412(3)
C26 H26A 0.9600
C26 H26B 0.9600
C26 H26C 0.9600
C27 C28 1.380(3)
C27 H27 0.9300
C28 H28 0.9300
N1 H1A 0.8600
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
N1 H1A O1 0.86 2.10 2.929(2) 161.6 3_676
