#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/14/7151419.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_7151419
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            'C28 H22 N2 O3 S'
_chemical_formula_weight         466.54
_chemical_melting_point          476.6(5)
_chemical_name_common
;
1-ethoxycarbonyl-2,3-dihydropyrolo(2,1-a)isoquinolin-3-yl-
(10H-phenothiazin-10-yl)-1-methanone
;
_chemical_name_systematic
; 
1-ethoxycarbonyl-2,3-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                 125.498(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.180(4)
_cell_length_b                   18.259(4)
_cell_length_c                   14.878(3)
_cell_measurement_temperature    293(2)
_cell_volume                     4463.1(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13018
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.180
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0501
_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)+(0.0796P)²+1.9291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2757
_reflns_number_total             3713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b302662k.txt
_cod_data_source_block           grandprm=_2c
_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 '203-204C' was changed to '476.6(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        4463.0(15)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7151419
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 0.32784(16) 0.05531(14) 0.7909(2) 0.0270(6) Uani 1 1 d . . .
C2 C 0.30337(18) 0.08436(14) 0.6797(2) 0.0275(6) Uani 1 1 d . . .
C3 C 0.30208(16) 0.01522(14) 0.6211(2) 0.0259(6) Uani 1 1 d . . .
N4 N 0.35742(13) -0.03309(11) 0.71334(17) 0.0267(5) Uani 1 1 d . . .
C5 C 0.38240(17) -0.09878(15) 0.6989(2) 0.0330(6) Uani 1 1 d . . .
C6 C 0.42066(18) -0.14730(15) 0.7815(2) 0.0362(7) Uani 1 1 d . . .
C7 C 0.43520(16) -0.13005(15) 0.8859(2) 0.0327(6) Uani 1 1 d . . .
C8 C 0.47664(18) -0.17955(17) 0.9751(2) 0.0400(7) Uani 1 1 d . . .
C9 C 0.49248(18) -0.16211(18) 1.0749(3) 0.0418(8) Uani 1 1 d . . .
C10 C 0.46981(18) -0.09499(18) 1.0906(2) 0.0411(8) Uani 1 1 d . . .
C11 C 0.42854(17) -0.04507(17) 1.0056(2) 0.0344(7) Uani 1 1 d . . .
C12 C 0.40938(16) -0.06235(14) 0.9016(2) 0.0283(6) Uani 1 1 d . . .
C13 C 0.36415(15) -0.01197(14) 0.8082(2) 0.0257(6) Uani 1 1 d . . .
O14 O 0.20384(11) -0.07498(10) 0.58878(15) 0.0343(5) Uani 1 1 d . . .
C15 C 0.21709(16) -0.02030(14) 0.5555(2) 0.0266(6) Uani 1 1 d . . .
N16 N 0.15594(13) 0.01583(11) 0.46116(17) 0.0259(5) Uani 1 1 d . . .
C17 C 0.07267(16) -0.00277(15) 0.4145(2) 0.0300(6) Uani 1 1 d . . .
C18 C 0.04444(18) -0.07378(17) 0.3847(2) 0.0352(7) Uani 1 1 d . . .
C19 C -0.0354(2) -0.0894(2) 0.3462(2) 0.0439(8) Uani 1 1 d . . .
C20 C -0.0863(2) -0.0343(2) 0.3356(2) 0.0444(8) Uani 1 1 d . . .
C21 C -0.05940(18) 0.03684(19) 0.3621(2) 0.0404(8) Uani 1 1 d . . .
C22 C 0.02094(17) 0.05307(16) 0.4028(2) 0.0349(7) Uani 1 1 d . . .
S23 S 0.05804(5) 0.14271(4) 0.44479(6) 0.0372(2) Uani 1 1 d . . .
C24 C 0.12682(16) 0.14426(14) 0.4079(2) 0.0293(6) Uani 1 1 d . . .
C25 C 0.13938(18) 0.20784(16) 0.3686(2) 0.0362(7) Uani 1 1 d . . .
C26 C 0.19303(18) 0.20823(16) 0.3402(2) 0.0363(7) Uani 1 1 d . . .
C27 C 0.23304(17) 0.14494(15) 0.3473(2) 0.0315(6) Uani 1 1 d . . .
C28 C 0.22063(17) 0.08074(16) 0.3857(2) 0.0291(6) Uani 1 1 d . . .
C29 C 0.16949(15) 0.08055(14) 0.41926(19) 0.0268(6) Uani 1 1 d . . .
C30 C 0.31174(17) 0.09812(14) 0.8566(2) 0.0332(6) Uani 1 1 d . . .
O31 O 0.31841(13) 0.08113(10) 0.94139(16) 0.0398(5) Uani 1 1 d . . .
O32 O 0.28136(14) 0.16481(10) 0.80882(17) 0.0453(6) Uani 1 1 d . . .
C33 C 0.2545(3) 0.21256(19) 0.8607(3) 0.0558(10) Uani 1 1 d . . .
H18 H 0.219(2) 0.192(2) 0.882(3) 0.067 Uiso 1 1 d . . .
H19 H 0.208(2) 0.2473(19) 0.797(3) 0.067 Uiso 1 1 d . . .
C34 C 0.3240(3) 0.2524(2) 0.9530(4) 0.0594(10) Uani 1 1 d . . .
H20 H 0.348(2) 0.278(2) 0.920(3) 0.071 Uiso 1 1 d . . .
H21 H 0.366(2) 0.212(2) 1.019(3) 0.071 Uiso 1 1 d . . .
H22 H 0.297(2) 0.291(2) 0.977(3) 0.071 Uiso 1 1 d . . .
H1 H 0.2540(18) 0.1059(15) 0.641(2) 0.029(7) Uiso 1 1 d . . .
H2 H 0.3437(15) 0.1213(14) 0.687(2) 0.023(6) Uiso 1 1 d . . .
H3 H 0.3193(15) 0.0198(13) 0.573(2) 0.023(6) Uiso 1 1 d . . .
H4 H 0.3713(17) -0.1076(15) 0.622(2) 0.040(8) Uiso 1 1 d . . .
H5 H 0.4430(17) -0.1958(15) 0.775(2) 0.039(8) Uiso 1 1 d . . .
H6 H 0.495(2) -0.2262(19) 0.961(3) 0.063(10) Uiso 1 1 d . . .
H7 H 0.522(2) -0.1975(18) 1.132(3) 0.056(10) Uiso 1 1 d . . .
H8 H 0.4801(18) -0.0786(16) 1.158(3) 0.046(9) Uiso 1 1 d . . .
H9 H 0.4164(16) 0.0032(16) 1.023(2) 0.028(7) Uiso 1 1 d . . .
H10 H 0.0789(15) -0.1118(14) 0.394(2) 0.021(7) Uiso 1 1 d . . .
H11 H -0.0535(16) -0.1377(15) 0.325(2) 0.026(7) Uiso 1 1 d . . .
H12 H -0.143(2) -0.0459(18) 0.308(3) 0.065(10) Uiso 1 1 d . . .
H13 H -0.0953(18) 0.0757(16) 0.356(2) 0.037(8) Uiso 1 1 d . . .
H14 H 0.1127(18) 0.2502(17) 0.363(2) 0.046(9) Uiso 1 1 d . . .
H15 H 0.2022(17) 0.2532(16) 0.314(2) 0.043(8) Uiso 1 1 d . . .
H16 H 0.2689(18) 0.1447(15) 0.324(2) 0.040(8) Uiso 1 1 d . . .
H17 H 0.2469(16) 0.0375(15) 0.393(2) 0.023(7) 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
C13 C1 C30 132.0(2) . . ?
C13 C1 C2 108.4(2) . . ?
C30 C1 C2 119.6(2) . . ?
C1 C2 C3 102.7(2) . . ?
N4 C3 C2 102.3(2) . . ?
N4 C3 C15 107.7(2) . . ?
C2 C3 C15 110.7(2) . . ?
C5 N4 C13 125.1(2) . . ?
C5 N4 C3 122.3(2) . . ?
C13 N4 C3 110.9(2) . . ?
C6 C5 N4 120.4(3) . . ?
C5 C6 C7 119.6(3) . . ?
C8 C7 C12 118.7(3) . . ?
C8 C7 C6 120.9(3) . . ?
C12 C7 C6 120.4(2) . . ?
C9 C8 C7 120.8(3) . . ?
C8 C9 C10 120.2(3) . . ?
C9 C10 C11 121.1(3) . . ?
C10 C11 C12 119.9(3) . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 C13 122.0(2) . . ?
C7 C12 C13 118.7(2) . . ?
C1 C13 N4 109.3(2) . . ?
C1 C13 C12 135.2(2) . . ?
N4 C13 C12 115.4(2) . . ?
O14 C15 N16 121.9(2) . . ?
O14 C15 C3 121.2(2) . . ?
N16 C15 C3 116.8(2) . . ?
C15 N16 C29 123.4(2) . . ?
C15 N16 C17 118.7(2) . . ?
C29 N16 C17 116.7(2) . . ?
C18 C17 C22 120.4(3) . . ?
C18 C17 N16 121.7(3) . . ?
C22 C17 N16 117.9(2) . . ?
C17 C18 C19 119.2(3) . . ?
C20 C19 C18 120.3(3) . . ?
C21 C20 C19 120.8(3) . . ?
C20 C21 C22 119.5(3) . . ?
C21 C22 C17 119.7(3) . . ?
C21 C22 S23 120.0(2) . . ?
C17 C22 S23 120.2(2) . . ?
C22 S23 C24 98.87(13) . . ?
C25 C24 C29 119.8(2) . . ?
C25 C24 S23 120.9(2) . . ?
C29 C24 S23 119.32(19) . . ?
C26 C25 C24 120.3(3) . . ?
C25 C26 C27 120.3(3) . . ?
C26 C27 C28 120.1(3) . . ?
C29 C28 C27 120.1(3) . . ?
C28 C29 C24 119.4(2) . . ?
C28 C29 N16 122.0(2) . . ?
C24 C29 N16 118.6(2) . . ?
O31 C30 O32 120.6(2) . . ?
O31 C30 C1 129.2(2) . . ?
O32 C30 C1 110.1(2) . . ?
C30 O32 C33 116.7(2) . . ?
O32 C33 C34 110.2(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
C1 C13 1.376(4) . ?
C1 C30 1.428(4) . ?
C1 C2 1.521(3) . ?
C2 C3 1.526(4) . ?
C3 N4 1.459(3) . ?
C3 C15 1.540(4) . ?
N4 C5 1.365(3) . ?
N4 C13 1.391(3) . ?
C5 C6 1.337(4) . ?
C6 C7 1.439(4) . ?
C7 C8 1.410(4) . ?
C7 C12 1.412(4) . ?
C8 C9 1.362(4) . ?
C9 C10 1.375(5) . ?
C10 C11 1.379(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.462(4) . ?
O14 C15 1.211(3) . ?
C15 N16 1.385(3) . ?
N16 C29 1.435(3) . ?
N16 C17 1.438(3) . ?
C17 C18 1.382(4) . ?
C17 C22 1.396(4) . ?
C18 C19 1.390(4) . ?
C19 C20 1.381(5) . ?
C20 C21 1.374(5) . ?
C21 C22 1.394(4) . ?
C22 S23 1.757(3) . ?
S23 C24 1.764(3) . ?
C24 C25 1.388(4) . ?
C24 C29 1.398(4) . ?
C25 C26 1.372(4) . ?
C26 C27 1.378(4) . ?
C27 C28 1.390(4) . ?
C28 C29 1.383(3) . ?
C30 O31 1.228(3) . ?
C30 O32 1.363(3) . ?
O32 C33 1.461(4) . ?
C33 C34 1.464(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9213139
