#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151418.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_7151418
loop_
_publ_author_name
'Elena Bâcu'
'Dalila Samson-Belei'
'Guy Nowogrocki'
'Axel Couture'
'Pierre Grandclaudon'
_publ_section_title
;
 Benzoindolizine derivatives of N-acylphenothiazine. Synthesis and
 characterization
;
_journal_issue                   13
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              2377
_journal_page_last               2382
_journal_paper_doi               10.1039/b302662k
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C29 H22 N2 O5 S'
_chemical_formula_weight         510.55
_chemical_melting_point          459.6(5)
_chemical_name_common
;
1,2-Di(methoxycarbonyl)-1,10b-dihydropyrolo(2,1-a)isoquinolin-
3-yl-(10H-phenothiazin-10-yl)-1-methanone
;
_chemical_name_systematic
; 
1,2-Di(methoxycarbonyl)-1,10b-dihydropyrolo[2,1-a]isoquinolin-3-yl-
(10H-phenothiazin-10-yl)-1-methanone 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 99.163(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   37.608(6)
_cell_length_b                   8.6937(14)
_cell_length_c                   15.053(3)
_cell_measurement_temperature    293(2)
_cell_volume                     4858.8(15)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14845
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .13
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0769P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                3206
_reflns_number_total             4155
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b302662k.txt
_cod_data_source_block           grandbtm=_1a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '186-187C' was changed to '459.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        4858.8(14)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7151418
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.17163(6) 0.8668(3) 0.80538(14) 0.0216(5) Uani 1 1 d . . .
C2 C 0.13174(6) 0.8752(2) 0.76861(15) 0.0223(5) Uani 1 1 d . . .
C3 C 0.12573(6) 0.8197(2) 0.68388(15) 0.0220(5) Uani 1 1 d . . .
N4 N 0.15678(5) 0.7646(2) 0.65835(12) 0.0217(4) Uani 1 1 d . . .
C5 C 0.16257(6) 0.6913(3) 0.58033(16) 0.0248(5) Uani 1 1 d . . .
C6 C 0.19615(6) 0.6535(3) 0.56981(16) 0.0255(5) Uani 1 1 d . . .
C7 C 0.22720(6) 0.7074(3) 0.63271(14) 0.0225(5) Uani 1 1 d . . .
C8 C 0.26210(6) 0.7076(3) 0.61190(17) 0.0263(5) Uani 1 1 d . . .
C9 C 0.29015(6) 0.7721(3) 0.67048(16) 0.0277(6) Uani 1 1 d . . .
C10 C 0.28428(6) 0.8393(3) 0.75029(17) 0.0270(5) Uani 1 1 d . . .
C11 C 0.24960(6) 0.8394(3) 0.77213(16) 0.0241(5) Uani 1 1 d . . .
C12 C 0.22139(6) 0.7722(3) 0.71498(15) 0.0224(5) Uani 1 1 d . . .
C13 C 0.18450(6) 0.7522(3) 0.73945(14) 0.0222(5) Uani 1 1 d . . .
O14 O 0.08099(4) 0.95131(18) 0.58547(11) 0.0297(4) Uani 1 1 d . . .
C15 C 0.09142(6) 0.8275(3) 0.61651(15) 0.0222(5) Uani 1 1 d . . .
N16 N 0.07444(5) 0.6908(2) 0.59186(12) 0.0209(4) Uani 1 1 d . . .
C17 C 0.08828(5) 0.5451(2) 0.62706(14) 0.0206(5) Uani 1 1 d . . .
C18 C 0.09569(6) 0.5167(3) 0.71852(15) 0.0229(5) Uani 1 1 d . . .
C19 C 0.11109(6) 0.3781(3) 0.74966(16) 0.0252(5) Uani 1 1 d . . .
C20 C 0.11790(6) 0.2662(3) 0.68869(16) 0.0265(5) Uani 1 1 d . . .
C21 C 0.10883(6) 0.2912(3) 0.59730(16) 0.0239(5) Uani 1 1 d . . .
C22 C 0.09418(6) 0.4312(3) 0.56573(15) 0.0218(5) Uani 1 1 d . . .
S23 S 0.082843(15) 0.46324(7) 0.44924(4) 0.02543(19) Uani 1 1 d . . .
C24 C 0.04530(6) 0.5861(3) 0.44999(15) 0.0236(5) Uani 1 1 d . . .
C25 C 0.01684(6) 0.5816(3) 0.37836(16) 0.0278(6) Uani 1 1 d . . .
C26 C -0.01177(6) 0.6820(3) 0.37688(17) 0.0303(6) Uani 1 1 d . . .
C27 C -0.01295(6) 0.7824(3) 0.44801(17) 0.0288(6) Uani 1 1 d . . .
C28 C 0.01497(6) 0.7842(3) 0.52014(17) 0.0253(5) Uani 1 1 d . . .
C29 C 0.04430(6) 0.6878(3) 0.52007(15) 0.0225(5) Uani 1 1 d . . .
C30 C 0.17865(6) 0.8078(3) 0.90139(16) 0.0270(5) Uani 1 1 d . . .
O31 O 0.16712(5) 0.6889(2) 0.92553(11) 0.0401(5) Uani 1 1 d . . .
O32 O 0.19984(5) 0.9037(2) 0.95480(11) 0.0361(4) Uani 1 1 d . . .
C33 C 0.20722(10) 0.8595(4) 1.04863(19) 0.0495(8) Uani 1 1 d . . .
H17 H 0.2147(8) 0.747(4) 1.052(2) 0.059 Uiso 1 1 d . . .
H18 H 0.1848(9) 0.860(4) 1.074(2) 0.059 Uiso 1 1 d . . .
H19 H 0.2255(9) 0.931(4) 1.073(2) 0.059 Uiso 1 1 d . . .
C34 C 0.10748(6) 0.9484(3) 0.82213(16) 0.0278(6) Uani 1 1 d . . .
O35 O 0.11751(5) 1.0212(2) 0.88930(12) 0.0413(5) Uani 1 1 d . . .
O36 O 0.07239(4) 0.9251(2) 0.78786(11) 0.0342(4) Uani 1 1 d . . .
C37 C 0.04767(8) 0.9999(4) 0.8387(2) 0.0463(8) Uani 1 1 d . . .
H20 H 0.0238(9) 0.963(3) 0.812(2) 0.056 Uiso 1 1 d . . .
H21 H 0.0534(8) 0.969(3) 0.901(2) 0.056 Uiso 1 1 d . . .
H22 H 0.0505(8) 1.116(4) 0.8339(19) 0.056 Uiso 1 1 d . . .
H1 H 0.1824(6) 0.969(3) 0.8001(14) 0.016(5) Uiso 1 1 d . . .
H2 H 0.1425(7) 0.674(3) 0.5358(17) 0.039(7) Uiso 1 1 d . . .
H3 H 0.2002(6) 0.601(3) 0.5157(16) 0.025(6) Uiso 1 1 d . . .
H4 H 0.2667(7) 0.659(3) 0.5559(18) 0.045(8) Uiso 1 1 d . . .
H5 H 0.3138(9) 0.767(3) 0.656(2) 0.059(9) Uiso 1 1 d . . .
H6 H 0.3043(7) 0.884(3) 0.7922(17) 0.035(7) Uiso 1 1 d . . .
H7 H 0.2460(6) 0.893(3) 0.8260(16) 0.024(6) Uiso 1 1 d . . .
H8 H 0.1817(6) 0.646(3) 0.7649(16) 0.033(7) Uiso 1 1 d . . .
H9 H 0.0906(6) 0.595(3) 0.7588(15) 0.016(5) Uiso 1 1 d . . .
H10 H 0.1169(7) 0.356(3) 0.8164(17) 0.035(7) Uiso 1 1 d . . .
H11 H 0.1283(6) 0.170(3) 0.7074(16) 0.030(7) Uiso 1 1 d . . .
H12 H 0.1130(6) 0.219(3) 0.5542(17) 0.030(7) Uiso 1 1 d . . .
H13 H 0.0171(6) 0.509(3) 0.3322(15) 0.018(6) Uiso 1 1 d . . .
H14 H -0.0327(7) 0.674(3) 0.3218(18) 0.041(7) Uiso 1 1 d . . .
H15 H -0.0331(6) 0.853(3) 0.4463(14) 0.023(6) Uiso 1 1 d . . .
H16 H 0.0132(6) 0.855(3) 0.5676(16) 0.026(6) Uiso 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'
S S 0.1246 0.1234 '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
C2 C1 C30 112.10(18) . . ?
C2 C1 C13 100.99(17) . . ?
C30 C1 C13 111.77(19) . . ?
C3 C2 C34 130.9(2) . . ?
C3 C2 C1 109.57(19) . . ?
C34 C2 C1 119.34(19) . . ?
C2 C3 N4 111.59(19) . . ?
C2 C3 C15 128.0(2) . . ?
N4 C3 C15 120.11(19) . . ?
C3 N4 C5 130.87(19) . . ?
C3 N4 C13 108.30(17) . . ?
C5 N4 C13 118.81(18) . . ?
C6 C5 N4 119.5(2) . . ?
C5 C6 C7 121.2(2) . . ?
C8 C7 C12 118.7(2) . . ?
C8 C7 C6 122.6(2) . . ?
C12 C7 C6 118.6(2) . . ?
C9 C8 C7 120.4(2) . . ?
C8 C9 C10 120.9(2) . . ?
C9 C10 C11 119.3(2) . . ?
C12 C11 C10 120.4(2) . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 C13 122.9(2) . . ?
C7 C12 C13 116.6(2) . . ?
N4 C13 C12 110.29(17) . . ?
N4 C13 C1 103.45(17) . . ?
C12 C13 C1 118.77(19) . . ?
O14 C15 N16 123.8(2) . . ?
O14 C15 C3 119.2(2) . . ?
N16 C15 C3 116.99(19) . . ?
C15 N16 C29 119.79(18) . . ?
C15 N16 C17 122.52(18) . . ?
C29 N16 C17 117.21(17) . . ?
C18 C17 C22 120.2(2) . . ?
C18 C17 N16 121.9(2) . . ?
C22 C17 N16 117.88(19) . . ?
C17 C18 C19 120.0(2) . . ?
C18 C19 C20 119.8(2) . . ?
C21 C20 C19 120.4(2) . . ?
C20 C21 C22 120.0(2) . . ?
C21 C22 C17 119.5(2) . . ?
C21 C22 S23 119.99(18) . . ?
C17 C22 S23 120.53(17) . . ?
C22 S23 C24 98.97(10) . . ?
C29 C24 C25 119.9(2) . . ?
C29 C24 S23 120.62(17) . . ?
C25 C24 S23 119.51(19) . . ?
C26 C25 C24 119.6(2) . . ?
C25 C26 C27 120.3(2) . . ?
C28 C27 C26 119.9(2) . . ?
C27 C28 C29 119.8(2) . . ?
C24 C29 C28 120.4(2) . . ?
C24 C29 N16 118.16(19) . . ?
C28 C29 N16 121.4(2) . . ?
O31 C30 O32 124.6(2) . . ?
O31 C30 C1 124.3(2) . . ?
O32 C30 C1 111.1(2) . . ?
C30 O32 C33 115.2(2) . . ?
O35 C34 O36 123.8(2) . . ?
O35 C34 C2 123.7(2) . . ?
O36 C34 C2 112.5(2) . . ?
C34 O36 C37 113.6(2) . . ?
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
C1 C2 1.516(3) . ?
C1 C30 1.517(3) . ?
C1 C13 1.538(3) . ?
C2 C3 1.349(3) . ?
C2 C34 1.456(3) . ?
C3 N4 1.372(3) . ?
C3 C15 1.511(3) . ?
N4 C5 1.384(3) . ?
N4 C13 1.478(3) . ?
C5 C6 1.338(3) . ?
C6 C7 1.459(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.409(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.385(4) . ?
C10 C11 1.395(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.501(3) . ?
O14 C15 1.213(3) . ?
C15 N16 1.372(3) . ?
N16 C29 1.436(3) . ?
N16 C17 1.438(3) . ?
C17 C18 1.383(3) . ?
C17 C22 1.396(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.389(3) . ?
C20 C21 1.381(3) . ?
C21 C22 1.388(3) . ?
C22 S23 1.760(2) . ?
S23 C24 1.772(2) . ?
C24 C29 1.381(3) . ?
C24 C25 1.394(3) . ?
C25 C26 1.383(4) . ?
C26 C27 1.387(4) . ?
C27 C28 1.385(3) . ?
C28 C29 1.386(3) . ?
C30 O31 1.199(3) . ?
C30 O32 1.332(3) . ?
O32 C33 1.447(3) . ?
C34 O35 1.202(3) . ?
C34 O36 1.353(3) . ?
O36 C37 1.449(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9235439
