#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/07/1520725.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_1520725
loop_
_publ_author_name
'Braun, Doris E.'
'Koztecki, Lien H.'
'McMahon, Jennifer A.'
'Price, Sarah L.'
'Reutzel-Edens, Susan M'
_publ_section_title
;
 Navigating the Waters of Unconventional Crystalline Hydrates.
;
_journal_issue                   8
_journal_name_full               'Molecular pharmaceutics'
_journal_page_first              3069
_journal_page_last               3088
_journal_paper_doi               10.1021/acs.molpharmaceut.5b00357
_journal_volume                  12
_journal_year                    2015
_chemical_formula_moiety         'C22  H25  N3  O3, H3.90 O1.95'
_chemical_formula_sum            'C22 H28.9 N3 O4.95'
_chemical_formula_weight         414.589
_chemical_name_systematic
;
 3-(4-dibenzo[b,f][1,4]oxepin-11-yl-piperazin-1-yl)-2,2-dimethylpropanoic acid 
Hydrate A 1.95
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-04-22T08:48:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 128.322(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.663(7)
_cell_length_b                   9.634(2)
_cell_length_c                   20.863(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     4204(2)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8-based 3-circle geometry'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7816
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.754
_diffrn_reflns_theta_min         1.947
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1772
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.06
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0441P)²+1.0254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                2331
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp5b00357_si_002.cif
_cod_data_source_block           HyA1.95
_cod_depositor_comments
'Adding full bibliography for 1520723--1520725.cif.'
_cod_original_cell_volume        4205(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C22 H28.90 N3 O4.95'
_cod_database_code               1520725
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_calc_flag
C1 C 0.21389(10) 0.4613(2) -0.04119(15) 0.0351(6) Uani 1 d
C2 C 0.27910(10) 0.5021(2) 0.03160(14) 0.0343(5) Uani 1 d
C3 C 0.31109(11) 0.4308(2) 0.10549(15) 0.0427(6) Uani 1 d
H3 H 0.2914 0.3525 0.1092 0.051 Uiso 1 calc
C4 C 0.37067(12) 0.4721(3) 0.17300(16) 0.0538(7) Uani 1 d
H4 H 0.3919 0.4224 0.2229 0.065 Uiso 1 calc
C5 C 0.39965(13) 0.5867(3) 0.16806(17) 0.0568(7) Uani 1 d
H5 H 0.4402 0.6173 0.2151 0.068 Uiso 1 calc
C6 C 0.36975(12) 0.6562(3) 0.09505(17) 0.0486(7) Uani 1 d
H6 H 0.3899 0.7336 0.0913 0.058 Uiso 1 calc
C7 C 0.31065(11) 0.6130(2) 0.02775(15) 0.0375(6) Uani 1 d
C8 C 0.27534(11) 0.6002(2) -0.10451(14) 0.0382(6) Uani 1 d
C9 C 0.31015(12) 0.6331(2) -0.13095(15) 0.0458(6) Uani 1 d
H9 H 0.3391 0.709 -0.1073 0.055 Uiso 1 calc
C10 C 0.30288(12) 0.5557(3) -0.19178(16) 0.0519(7) Uani 1 d
H10 H 0.3266 0.5783 -0.2104 0.062 Uiso 1 calc
C11 C 0.26092(12) 0.4452(3) -0.22550(15) 0.0483(7) Uani 1 d
H11 H 0.2558 0.3917 -0.2675 0.058 Uiso 1 calc
C12 C 0.22633(11) 0.4119(2) -0.19856(14) 0.0426(6) Uani 1 d
H12 H 0.1973 0.3361 -0.2227 0.051 Uiso 1 calc
C13 C 0.23346(10) 0.4880(2) -0.13650(14) 0.0372(6) Uani 1 d
C14 C 0.16987(11) 0.4883(2) 0.03403(14) 0.0383(6) Uani 1 d
H14A H 0.1388 0.5655 0.0058 0.046 Uiso 1 calc
H14B H 0.2121 0.5284 0.0783 0.046 Uiso 1 calc
C15 C 0.14908(10) 0.3911(2) 0.07018(14) 0.0374(6) Uani 1 d
H15A H 0.1818 0.3181 0.102 0.045 Uiso 1 calc
H15B H 0.1453 0.4433 0.1079 0.045 Uiso 1 calc
C16 C 0.09003(11) 0.2585(2) -0.05708(15) 0.0416(6) Uani 1 d
H16A H 0.0474 0.2219 -0.1025 0.05 Uiso 1 calc
H16B H 0.12 0.1791 -0.0314 0.05 Uiso 1 calc
C17 C 0.11188(11) 0.3579(2) -0.09090(15) 0.0425(6) Uani 1 d
H17A H 0.115 0.309 -0.13 0.051 Uiso 1 calc
H17B H 0.0804 0.4341 -0.1204 0.051 Uiso 1 calc
C18 C 0.06512(11) 0.2167(2) 0.03536(15) 0.0402(6) Uani 1 d
H18A H 0.1 0.1476 0.0665 0.048 Uiso 1 calc
H18B H 0.0279 0.1682 -0.0131 0.048 Uiso 1 calc
C19 C 0.04644(11) 0.2592(2) 0.08906(15) 0.0382(6) Uani 1 d
C20 C -0.00811(12) 0.3678(2) 0.04467(17) 0.0392(6) Uani 1 d
C21 C 0.10284(12) 0.3035(3) 0.17564(16) 0.0528(7) Uani 1 d
H21A H 0.1161 0.3976 0.1744 0.079 Uiso 1 calc
H21B H 0.1386 0.2392 0.1975 0.079 Uiso 1 calc
H21C H 0.09 0.3021 0.2106 0.079 Uiso 1 calc
C22 C 0.01685(13) 0.1269(2) 0.09505(18) 0.0570(8) Uani 1 d
H22A H 0.004 0.1456 0.1292 0.086 Uiso 1 calc
H22B H 0.0485 0.0518 0.1195 0.086 Uiso 1 calc
H22C H -0.0207 0.0993 0.0403 0.086 Uiso 1 calc
O1 O 0.28144(8) 0.68481(15) -0.04550(10) 0.0433(4) Uani 1 d
O2 O -0.00792(8) 0.45745(17) 0.08869(11) 0.0578(5) Uani 1 d
O3 O -0.05012(8) 0.35788(19) -0.02983(11) 0.0613(5) Uani 1 d
N1 N 0.19378(9) 0.45446(18) -0.11558(12) 0.0393(5) Uani 1 d
N2 N 0.17412(8) 0.41502(18) -0.02415(11) 0.0375(5) Uani 1 d
N3 N 0.08638(9) 0.32515(19) 0.00497(11) 0.0326(5) Uani 1 d
H1 H 0.0553(10) 0.399(2) -0.0244(13) 0.037(6) Uiso 1 d
O4B O 0.0762(8) 0.7830(10) 0.1645(7) 0.066(3) Uani 0.463(7) d
H41B H 0.074(5) 0.759(8) 0.124(4) 0.1 Uiso 0.463(7) d
H42B H 0.073(9) 0.727(8) 0.192(7) 0.1 Uiso 0.463(7) d
O4A O 0.0729(10) 0.7251(12) 0.1715(10) 0.125(5) Uani 0.518(5) d
H41A H 0.074(7) 0.712(10) 0.133(6) 0.187 Uiso 0.518(5) d
H42A H 0.081(7) 0.666(9) 0.205(6) 0.187 Uiso 0.518(5) d
O5 O 0.05746(18) 0.5667(4) 0.2354(2) 0.0662(15) Uani 0.518(5) d
H51 H 0.044(2) 0.516(5) 0.194(2) 0.099 Uiso 0.518(5) d
H52 H 0.0925(16) 0.551(6) 0.2802(17) 0.099 Uiso 0.518(5) d
O6 O 0.0031(3) 0.3588(4) 0.2311(4) 0.079(2) Uani 0.449(5) d
H61 H 0.008(4) 0.371(5) 0.195(4) 0.118 Uiso 0.449(5) d
H62 H 0 0.433(2) 0.25 0.118 Uiso 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 0 '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 0.006 '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
N1 C1 N2 118.6(2) .
N1 C1 C2 126.3(2) .
N2 C1 C2 114.8(2) .
C7 C2 C3 117.7(2) .
C7 C2 C1 120.6(2) .
C3 C2 C1 121.7(2) .
C4 C3 C2 121.1(2) .
C4 C3 H3 119.5 .
C2 C3 H3 119.5 .
C3 C4 C5 119.8(2) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
C6 C5 C4 120.1(3) .
C6 C5 H5 119.9 .
C4 C5 H5 119.9 .
C7 C6 C5 119.6(2) .
C7 C6 H6 120.2 .
C5 C6 H6 120.2 .
C6 C7 C2 121.7(2) .
C6 C7 O1 118.5(2) .
C2 C7 O1 119.8(2) .
C9 C8 C13 121.7(2) .
C9 C8 O1 118.6(2) .
C13 C8 O1 119.68(19) .
C10 C9 C8 119.9(2) .
C10 C9 H9 120 .
C8 C9 H9 120 .
C9 C10 C11 119.6(2) .
C9 C10 H10 120.2 .
C11 C10 H10 120.2 .
C10 C11 C12 120.4(2) .
C10 C11 H11 119.8 .
C12 C11 H11 119.8 .
C11 C12 C13 120.9(2) .
C11 C12 H12 119.5 .
C13 C12 H12 119.5 .
C8 C13 C12 117.4(2) .
C8 C13 N1 124.3(2) .
C12 C13 N1 118.1(2) .
N2 C14 C15 110.83(17) .
N2 C14 H14A 109.5 .
C15 C14 H14A 109.5 .
N2 C14 H14B 109.5 .
C15 C14 H14B 109.5 .
H14A C14 H14B 108.1 .
N3 C15 C14 111.10(18) .
N3 C15 H15A 109.4 .
C14 C15 H15A 109.4 .
N3 C15 H15B 109.4 .
C14 C15 H15B 109.4 .
H15A C15 H15B 108 .
N3 C16 C17 112.50(17) .
N3 C16 H16A 109.1 .
C17 C16 H16A 109.1 .
N3 C16 H16B 109.1 .
C17 C16 H16B 109.1 .
H16A C16 H16B 107.8 .
N2 C17 C16 109.5(2) .
N2 C17 H17A 109.8 .
C16 C17 H17A 109.8 .
N2 C17 H17B 109.8 .
C16 C17 H17B 109.8 .
H17A C17 H17B 108.2 .
N3 C18 C19 119.96(18) .
N3 C18 H18A 107.3 .
C19 C18 H18A 107.3 .
N3 C18 H18B 107.3 .
C19 C18 H18B 107.3 .
H18A C18 H18B 106.9 .
C21 C19 C18 114.18(18) .
C21 C19 C22 108.2(2) .
C18 C19 C22 104.57(18) .
C21 C19 C20 112.91(19) .
C18 C19 C20 110.67(19) .
C22 C19 C20 105.57(18) .
O3 C20 O2 124.2(2) .
O3 C20 C19 118.9(2) .
O2 C20 C19 116.7(2) .
C19 C21 H21A 109.5 .
C19 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C19 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C19 C22 H22A 109.5 .
C19 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C19 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C7 O1 C8 110.87(16) .
C1 N1 C13 121.9(2) .
C1 N2 C17 118.38(19) .
C1 N2 C14 121.42(17) .
C17 N2 C14 110.18(16) .
C15 N3 C16 109.46(16) .
C15 N3 C18 114.42(18) .
C16 N3 C18 108.02(16) .
C15 N3 H1 107.3(12) .
C16 N3 H1 104.9(12) .
C18 N3 H1 112.3(12) .
O4A O4B H41B 94(6) .
O4A O4B H42B 29(7) .
H41B O4B H42B 123(4) .
O4A O4B H41A 62(5) .
H41B O4B H41A 32(8) .
H42B O4B H41A 91(9) .
O4A O4B H42A 18(5) .
H41B O4B H42A 109(8) .
H42B O4B H42A 17(10) .
H41A O4B H42A 77(3) .
O4B O4A H41B 52(4) .
O4B O4A H42B 107(10) .
H41B O4A H42B 159(10) .
O4B O4A H41A 79(8) .
H41B O4A H41A 27(9) .
H42B O4A H41A 173(10) .
O4B O4A H42A 149(9) .
H41B O4A H42A 151(10) .
H42B O4A H42A 48(10) .
H41A O4A H42A 126(5) .
H42A O5 H51 88(5) .
H42A O5 H52 97(7) .
H51 O5 H52 121(4) .
O6 O6 H61 172(3) 2
O6 O6 H62 57.7(9) 2
H61 O6 H62 115(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.292(3) .
C1 N2 1.385(3) .
C1 C2 1.486(3) .
C2 C7 1.392(3) .
C2 C3 1.395(3) .
C3 C4 1.375(3) .
C3 H3 0.95 .
C4 C5 1.387(4) .
C4 H4 0.95 .
C5 C6 1.378(4) .
C5 H5 0.95 .
C6 C7 1.373(3) .
C6 H6 0.95 .
C7 O1 1.394(3) .
C8 C9 1.379(3) .
C8 C13 1.391(3) .
C8 O1 1.399(3) .
C9 C10 1.378(3) .
C9 H9 0.95 .
C10 C11 1.380(3) .
C10 H10 0.95 .
C11 C12 1.383(3) .
C11 H11 0.95 .
C12 C13 1.395(3) .
C12 H12 0.95 .
C13 N1 1.410(3) .
C14 N2 1.468(3) .
C14 C15 1.507(3) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 N3 1.493(3) .
C15 H15A 0.99 .
C15 H15B 0.99 .
C16 N3 1.502(3) .
C16 C17 1.505(3) .
C16 H16A 0.99 .
C16 H16B 0.99 .
C17 N2 1.459(3) .
C17 H17A 0.99 .
C17 H17B 0.99 .
C18 N3 1.504(3) .
C18 C19 1.537(3) .
C18 H18A 0.99 .
C18 H18B 0.99 .
C19 C21 1.529(3) .
C19 C22 1.545(3) .
C19 C20 1.548(3) .
C20 O3 1.233(3) .
C20 O2 1.259(3) .
C21 H21A 0.98 .
C21 H21B 0.98 .
C21 H21C 0.98 .
C22 H22A 0.98 .
C22 H22B 0.98 .
C22 H22C 0.98 .
N3 H1 0.97(2) .
O4B O4A 0.597(18) .
O4B H41B 0.84(2) .
O4B H42B 0.82(2) .
O4B H41A 0.92(8) .
O4B H42A 1.37(5) .
O4A H41B 1.06(5) .
O4A H42B 0.42(7) .
O4A H41A 0.83(2) .
O4A H42A 0.82(2) .
O5 H42A 1.48(8) .
O5 H51 0.855(19) .
O5 H52 0.830(19) .
O6 O6 0.900(8) 2
O6 H61 0.858(19) .
O6 H62 0.841(19) .
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
N1 C1 C2 C7 41.8(3)
N2 C1 C2 C7 -144.3(2)
N1 C1 C2 C3 -137.5(2)
N2 C1 C2 C3 36.4(3)
C7 C2 C3 C4 2.5(3)
C1 C2 C3 C4 -178.1(2)
C2 C3 C4 C5 0.2(4)
C3 C4 C5 C6 -2.1(4)
C4 C5 C6 C7 1.2(4)
C5 C6 C7 C2 1.6(3)
C5 C6 C7 O1 -179.8(2)
C3 C2 C7 C6 -3.4(3)
C1 C2 C7 C6 177.2(2)
C3 C2 C7 O1 178.03(19)
C1 C2 C7 O1 -1.3(3)
C13 C8 C9 C10 1.4(4)
O1 C8 C9 C10 -176.9(2)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 C12 -0.1(4)
C10 C11 C12 C13 -0.6(4)
C9 C8 C13 C12 -2.0(3)
O1 C8 C13 C12 176.30(19)
C9 C8 C13 N1 -175.9(2)
O1 C8 C13 N1 2.3(3)
C11 C12 C13 C8 1.6(3)
C11 C12 C13 N1 175.9(2)
N2 C14 C15 N3 -57.4(2)
N3 C16 C17 N2 57.5(2)
N3 C18 C19 C21 -71.4(3)
N3 C18 C19 C22 170.5(2)
N3 C18 C19 C20 57.3(3)
C21 C19 C20 O3 165.9(2)
C18 C19 C20 O3 36.5(3)
C22 C19 C20 O3 -76.1(3)
C21 C19 C20 O2 -17.4(3)
C18 C19 C20 O2 -146.8(2)
C22 C19 C20 O2 100.6(2)
C6 C7 O1 C8 114.5(2)
C2 C7 O1 C8 -66.9(2)
C9 C8 O1 C7 -113.3(2)
C13 C8 O1 C7 68.4(3)
N2 C1 N1 C13 -174.32(18)
C2 C1 N1 C13 -0.7(3)
C8 C13 N1 C1 -41.6(3)
C12 C13 N1 C1 144.5(2)
N1 C1 N2 C17 1.3(3)
C2 C1 N2 C17 -173.08(18)
N1 C1 N2 C14 -140.8(2)
C2 C1 N2 C14 44.8(3)
C16 C17 N2 C1 154.30(18)
C16 C17 N2 C14 -59.6(2)
C15 C14 N2 C1 -154.7(2)
C15 C14 N2 C17 60.4(2)
C14 C15 N3 C16 53.3(2)
C14 C15 N3 C18 174.65(17)
C17 C16 N3 C15 -54.0(2)
C17 C16 N3 C18 -179.21(19)
C19 C18 N3 C15 67.8(3)
C19 C18 N3 C16 -170.05(19)
