#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:35:54 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244545 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/91/7239100.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_7239100
loop_
_publ_author_name
'Blumberg, Laura C.'
'Zeidan, Tarek A.'
'Maddaford, Adrian'
'Warren, Nicole C.'
'Hutchison, Panee'
_publ_section_title
;
 Novel N-5-(acyloxyalkoxy)carbonyl prodrugs of olanzapine with
 physicochemical properties for extended-release
;
_journal_issue                   37
_journal_name_full               'RSC Advances'
_journal_page_first              16270
_journal_paper_doi               10.1039/c3ra41967c
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C25 H32 N4 O4 S'
_chemical_formula_sum            'C25 H32 N4 O4 S'
_chemical_formula_weight         484.61
_chemical_melting_point          328
_chemical_name_systematic
;
(palmitoyloxy) methyl
2-methyl-4-(4-methylpiperazin-1-yl)-4H-benzo[b]thieno[2,3-e][1,4]diazepine-5-carboxylate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2013-02-12 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.795(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5728(2)
_cell_length_b                   14.8243(3)
_cell_length_c                   16.8046(3)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      61.63
_cell_measurement_theta_min      4.33
_cell_volume                     2546.53(8)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17085
_diffrn_reflns_theta_full        69.48
_diffrn_reflns_theta_max         69.48
_diffrn_reflns_theta_min         4.04
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_T_max  0.7933
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00095(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0850P)²+0.0700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                3200
_reflns_number_total             4476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41967c.txt
_cod_data_source_block           3bh(C16)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7239100
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 -0.1662(3) 0.30785(15) 0.28110(15) 0.0424(6) Uani 1 1 d .
C2 C -0.2564(3) 0.33063(16) 0.32544(17) 0.0488(6) Uani 1 1 d .
H2A H -0.2495 0.3052 0.3783 0.059 Uiso 1 1 calc R
C3 C -0.3557(3) 0.39031(18) 0.29201(18) 0.0543(7) Uani 1 1 d .
H3A H -0.4175 0.4064 0.3218 0.065 Uiso 1 1 calc R
C4 C -0.3652(3) 0.42691(18) 0.21429(18) 0.0555(7) Uani 1 1 d .
H4A H -0.4324 0.4692 0.1918 0.067 Uiso 1 1 calc R
C5 C -0.2779(3) 0.40216(17) 0.16977(18) 0.0522(7) Uani 1 1 d .
H5A H -0.2859 0.4278 0.1169 0.063 Uiso 1 1 calc R
C6 C -0.1777(3) 0.34011(15) 0.20081(16) 0.0446(6) Uani 1 1 d .
C7 C -0.0345(2) 0.24047(15) 0.15702(14) 0.0406(5) Uani 1 1 d .
C8 C 0.0782(3) 0.10578(16) 0.10997(15) 0.0423(6) Uani 1 1 d .
C9 C 0.0377(3) 0.08671(15) 0.17712(15) 0.0427(6) Uani 1 1 d .
H9A H 0.0471 0.0285 0.2016 0.051 Uiso 1 1 calc R
C10 C -0.0215(2) 0.16144(14) 0.20997(14) 0.0393(5) Uani 1 1 d .
C11 C -0.0525(2) 0.16612(14) 0.28531(14) 0.0377(5) Uani 1 1 d .
C12 C -0.1084(3) 0.00632(15) 0.30018(15) 0.0436(6) Uani 1 1 d .
H12A H -0.0290 -0.0312 0.3191 0.052 Uiso 1 1 calc R
H12B H -0.1328 0.0069 0.2393 0.052 Uiso 1 1 calc R
C13 C -0.2193(3) -0.03372(17) 0.33106(15) 0.0487(6) Uani 1 1 d .
H13A H -0.3012 -0.0006 0.3063 0.058 Uiso 1 1 calc R
H13B H -0.2323 -0.0975 0.3134 0.058 Uiso 1 1 calc R
C14 C -0.1781(3) 0.06493(17) 0.44570(16) 0.0477(6) Uani 1 1 d .
H14A H -0.1633 0.0689 0.5062 0.057 Uiso 1 1 calc R
H14B H -0.2594 0.0983 0.4199 0.057 Uiso 1 1 calc R
C15 C -0.0647(3) 0.10672(17) 0.42047(14) 0.0465(6) Uani 1 1 d .
H15A H -0.0577 0.1712 0.4363 0.056 Uiso 1 1 calc R
H15B H 0.0173 0.0763 0.4498 0.056 Uiso 1 1 calc R
C16 C -0.2947(3) -0.0729(2) 0.45068(18) 0.0635(8) Uani 1 1 d .
H16A H -0.3028 -0.1361 0.4330 0.095 Uiso 1 1 calc R
H16B H -0.3781 -0.0418 0.4285 0.095 Uiso 1 1 calc R
H16C H -0.2718 -0.0701 0.5109 0.095 Uiso 1 1 calc R
C17 C 0.1509(3) 0.04643(17) 0.06460(16) 0.0514(7) Uani 1 1 d .
H17A H 0.1629 -0.0134 0.0902 0.077 Uiso 1 1 calc R
H17B H 0.2366 0.0730 0.0669 0.077 Uiso 1 1 calc R
H17C H 0.1009 0.0409 0.0071 0.077 Uiso 1 1 calc R
C18 C 0.0607(3) 0.29939(15) 0.35360(14) 0.0426(6) Uani 1 1 d .
C19 C 0.2857(3) 0.27530(18) 0.40353(16) 0.0510(6) Uani 1 1 d .
H19A H 0.2842 0.3354 0.4290 0.061 Uiso 1 1 calc R
H19B H 0.3447 0.2356 0.4440 0.061 Uiso 1 1 calc R
C20 C 0.3895(3) 0.20815(17) 0.30935(17) 0.0512(7) Uani 1 1 d .
C21 C 0.4060(3) 0.21851(19) 0.22489(17) 0.0527(7) Uani 1 1 d .
H21A H 0.4345 0.2810 0.2180 0.063 Uiso 1 1 calc R
H21B H 0.3202 0.2093 0.1850 0.063 Uiso 1 1 calc R
C22 C 0.5045(3) 0.15340(19) 0.20446(18) 0.0558(7) Uani 1 1 d .
H22A H 0.5890 0.1594 0.2463 0.067 Uiso 1 1 calc R
H22B H 0.4730 0.0908 0.2069 0.067 Uiso 1 1 calc R
C23 C 0.5254(3) 0.1707(2) 0.12003(19) 0.0604(8) Uani 1 1 d .
H23A H 0.5528 0.2341 0.1170 0.072 Uiso 1 1 calc R
H23B H 0.4412 0.1624 0.0783 0.072 Uiso 1 1 calc R
C24 C 0.6269(4) 0.1095(3) 0.0991(2) 0.0825(11) Uani 1 1 d .
H24A H 0.7092 0.1138 0.1432 0.099 Uiso 1 1 calc R
H24B H 0.5960 0.0463 0.0971 0.099 Uiso 1 1 calc R
C25 C 0.6535(4) 0.1328(4) 0.0194(3) 0.1191(17) Uani 1 1 d .
H25A H 0.7192 0.0914 0.0084 0.179 Uiso 1 1 calc R
H25B H 0.6862 0.1948 0.0216 0.179 Uiso 1 1 calc R
H25C H 0.5725 0.1277 -0.0245 0.179 Uiso 1 1 calc R
N1 N -0.0541(2) 0.25522(12) 0.31927(12) 0.0394(5) Uani 1 1 d .
N2 N -0.0976(2) 0.31694(13) 0.15082(13) 0.0448(5) Uani 1 1 d .
N3 N -0.0811(2) 0.09884(12) 0.33144(12) 0.0397(5) Uani 1 1 d .
N4 N -0.1924(2) -0.02909(14) 0.42024(12) 0.0453(5) Uani 1 1 d .
O1 O 0.07268(18) 0.37985(11) 0.36126(11) 0.0499(5) Uani 1 1 d .
O2 O 0.15790(18) 0.23839(11) 0.38169(10) 0.0446(4) Uani 1 1 d .
O3 O 0.33150(19) 0.28315(12) 0.33170(11) 0.0513(5) Uani 1 1 d .
O4 O 0.4218(2) 0.14496(14) 0.35487(13) 0.0757(7) Uani 1 1 d .
S1 S 0.04266(7) 0.21733(4) 0.07740(4) 0.0477(2) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 C1 C6 121.8(3)
C2 C1 N1 119.7(2)
C6 C1 N1 118.3(2)
C3 C2 C1 119.5(3)
C3 C2 H2A 120.3
C1 C2 H2A 120.3
C2 C3 C4 119.8(3)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 120.5(3)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C4 C5 C6 121.4(3)
C4 C5 H5A 119.3
C6 C5 H5A 119.3
N2 C6 C5 117.4(2)
N2 C6 C1 125.7(2)
C5 C6 C1 116.9(2)
N2 C7 C10 135.5(2)
N2 C7 S1 115.64(17)
C10 C7 S1 108.44(17)
C9 C8 C17 128.5(2)
C9 C8 S1 112.00(18)
C17 C8 S1 119.47(18)
C8 C9 C10 115.0(2)
C8 C9 H9A 122.5
C10 C9 H9A 122.5
C11 C10 C9 127.7(2)
C11 C10 C7 120.6(2)
C9 C10 C7 111.4(2)
N3 C11 C10 129.0(2)
N3 C11 N1 115.1(2)
C10 C11 N1 115.86(19)
N3 C12 C13 109.9(2)
N3 C12 H12A 109.7
C13 C12 H12A 109.7
N3 C12 H12B 109.7
C13 C12 H12B 109.7
H12A C12 H12B 108.2
N4 C13 C12 111.6(2)
N4 C13 H13A 109.3
C12 C13 H13A 109.3
N4 C13 H13B 109.3
C12 C13 H13B 109.3
H13A C13 H13B 108.0
N4 C14 C15 110.0(2)
N4 C14 H14A 109.7
C15 C14 H14A 109.7
N4 C14 H14B 109.7
C15 C14 H14B 109.7
H14A C14 H14B 108.2
N3 C15 C14 111.1(2)
N3 C15 H15A 109.4
C14 C15 H15A 109.4
N3 C15 H15B 109.4
C14 C15 H15B 109.4
H15A C15 H15B 108.0
N4 C16 H16A 109.5
N4 C16 H16B 109.5
H16A C16 H16B 109.5
N4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 C17 H17A 109.5
C8 C17 H17B 109.5
H17A C17 H17B 109.5
C8 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O1 C18 O2 125.0(3)
O1 C18 N1 125.2(2)
O2 C18 N1 109.75(19)
O3 C19 O2 108.8(2)
O3 C19 H19A 109.9
O2 C19 H19A 109.9
O3 C19 H19B 109.9
O2 C19 H19B 109.9
H19A C19 H19B 108.3
O4 C20 O3 122.2(3)
O4 C20 C21 127.3(3)
O3 C20 C21 110.5(2)
C20 C21 C22 113.9(2)
C20 C21 H21A 108.8
C22 C21 H21A 108.8
C20 C21 H21B 108.8
C22 C21 H21B 108.8
H21A C21 H21B 107.7
C23 C22 C21 112.1(2)
C23 C22 H22A 109.2
C21 C22 H22A 109.2
C23 C22 H22B 109.2
C21 C22 H22B 109.2
H22A C22 H22B 107.9
C22 C23 C24 113.5(3)
C22 C23 H23A 108.9
C24 C23 H23A 108.9
C22 C23 H23B 108.9
C24 C23 H23B 108.9
H23A C23 H23B 107.7
C25 C24 C23 112.3(3)
C25 C24 H24A 109.1
C23 C24 H24A 109.1
C25 C24 H24B 109.1
C23 C24 H24B 109.1
H24A C24 H24B 107.9
C24 C25 H25A 109.5
C24 C25 H25B 109.5
H25A C25 H25B 109.5
C24 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C18 N1 C1 118.22(19)
C18 N1 C11 120.4(2)
C1 N1 C11 114.5(2)
C7 N2 C6 123.2(2)
C11 N3 C15 122.95(19)
C11 N3 C12 122.59(19)
C15 N3 C12 113.58(18)
C13 N4 C14 109.06(19)
C13 N4 C16 111.9(2)
C14 N4 C16 110.7(2)
C18 O2 C19 114.8(2)
C20 O3 C19 116.3(2)
C8 S1 C7 92.87(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.393(3)
C1 C6 1.407(3)
C1 N1 1.427(3)
C2 C3 1.378(4)
C2 H2A 0.9500
C3 C4 1.394(4)
C3 H3A 0.9500
C4 C5 1.378(4)
C4 H4A 0.9500
C5 C6 1.400(4)
C5 H5A 0.9500
C6 N2 1.380(3)
C7 N2 1.306(3)
C7 C10 1.456(3)
C7 S1 1.769(2)
C8 C9 1.335(3)
C8 C17 1.499(3)
C8 S1 1.752(2)
C9 C10 1.449(3)
C9 H9A 0.9500
C10 C11 1.388(3)
C11 N3 1.344(3)
C11 N1 1.441(3)
C12 N3 1.471(3)
C12 C13 1.519(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 N4 1.454(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 N4 1.455(3)
C14 C15 1.503(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 N3 1.466(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 N4 1.461(3)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 O1 1.203(3)
C18 O2 1.360(3)
C18 N1 1.370(3)
C19 O3 1.416(3)
C19 O2 1.416(3)
C19 H19A 0.9900
C19 H19B 0.9900
C20 O4 1.202(3)
C20 O3 1.368(3)
C20 C21 1.482(4)
C21 C22 1.522(4)
C21 H21A 0.9900
C21 H21B 0.9900
C22 C23 1.512(4)
C22 H22A 0.9900
C22 H22B 0.9900
C23 C24 1.514(4)
C23 H23A 0.9900
C23 H23B 0.9900
C24 C25 1.478(5)
C24 H24A 0.9900
C24 H24B 0.9900
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -3.7(4)
N1 C1 C2 C3 172.2(2)
C1 C2 C3 C4 0.2(4)
C2 C3 C4 C5 1.6(4)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 N2 177.8(2)
C4 C5 C6 C1 -3.2(4)
C2 C1 C6 N2 -176.0(2)
N1 C1 C6 N2 8.1(4)
C2 C1 C6 C5 5.1(4)
N1 C1 C6 C5 -170.8(2)
C17 C8 C9 C10 175.4(3)
S1 C8 C9 C10 -2.1(3)
C8 C9 C10 C11 -168.6(3)
C8 C9 C10 C7 5.2(3)
N2 C7 C10 C11 -19.2(5)
S1 C7 C10 C11 168.6(2)
N2 C7 C10 C9 166.5(3)
S1 C7 C10 C9 -5.7(3)
C9 C10 C11 N3 -26.7(4)
C7 C10 C11 N3 160.1(3)
C9 C10 C11 N1 153.0(2)
C7 C10 C11 N1 -20.2(4)
N3 C12 C13 N4 -54.6(3)
N4 C14 C15 N3 57.1(3)
O4 C20 C21 C22 -16.9(4)
O3 C20 C21 C22 162.4(2)
C20 C21 C22 C23 -175.9(2)
C21 C22 C23 C24 177.7(3)
C22 C23 C24 C25 -175.2(3)
O1 C18 N1 C1 7.4(4)
O2 C18 N1 C1 -175.83(19)
O1 C18 N1 C11 156.9(2)
O2 C18 N1 C11 -26.3(3)
C2 C1 N1 C18 -95.9(3)
C6 C1 N1 C18 80.1(3)
C2 C1 N1 C11 112.8(2)
C6 C1 N1 C11 -71.2(3)
N3 C11 N1 C18 105.0(3)
C10 C11 N1 C18 -74.8(3)
N3 C11 N1 C1 -104.4(3)
C10 C11 N1 C1 75.8(3)
C10 C7 N2 C6 -0.9(5)
S1 C7 N2 C6 170.9(2)
C5 C6 N2 C7 -154.6(3)
C1 C6 N2 C7 26.5(4)
C10 C11 N3 C15 156.5(3)
N1 C11 N3 C15 -23.2(3)
C10 C11 N3 C12 -12.0(4)
N1 C11 N3 C12 168.2(2)
C14 C15 N3 C11 138.4(2)
C14 C15 N3 C12 -52.1(3)
C13 C12 N3 C11 -140.4(2)
C13 C12 N3 C15 50.0(3)
C12 C13 N4 C14 61.0(3)
C12 C13 N4 C16 -176.2(2)
C15 C14 N4 C13 -61.6(3)
C15 C14 N4 C16 175.0(2)
O1 C18 O2 C19 -15.2(3)
N1 C18 O2 C19 168.04(19)
O3 C19 O2 C18 -83.8(2)
O4 C20 O3 C19 -13.2(4)
C21 C20 O3 C19 167.5(2)
O2 C19 O3 C20 -85.8(3)
C9 C8 S1 C7 -1.2(2)
C17 C8 S1 C7 -178.9(2)
N2 C7 S1 C8 -170.0(2)
C10 C7 S1 C8 3.94(19)
