#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/07/1520724.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_1520724
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, H3.46 O1.73'
_chemical_formula_sum            'C22 H28.46 N3 O4.73'
_chemical_formula_weight         410.625
_chemical_name_systematic
;
 3-(4-dibenzo[b,f][1,4]oxepin-11-yl-piperazin-1-yl)-2,2-dimethylpropanoic acid 
Hydrate A 1.73
;
_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             2015-04-22T08:23:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 128.706(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.498(3)
_cell_length_b                   9.6469(8)
_cell_length_c                   20.342(3)
_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                     4057.8(9)
_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 0.765
_diffrn_measured_fraction_theta_max 0.809
_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  0.0462
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8478
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.722
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1754
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     321
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0707P)²+3.2707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                1811
_reflns_number_total             2810
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp5b00357_si_002.cif
_cod_data_source_block           HyA1.73
_cod_depositor_comments
'Adding full bibliography for 1520723--1520725.cif.'
_cod_original_cell_volume        4057.9(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1520724
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 0.21417(16) 0.4611(3) -0.0458(2) 0.0288(9) Uani 1 d
C2 C 0.28044(16) 0.5032(3) 0.0295(2) 0.0271(9) Uani 1 d
C3 C 0.31344(16) 0.4305(3) 0.1055(2) 0.0311(9) Uani 1 d
H3 H 0.2942 0.3505 0.1088 0.037 Uiso 1 calc
C4 C 0.37351(17) 0.4734(3) 0.1757(2) 0.0346(10) Uani 1 d
H4 H 0.3955 0.4233 0.227 0.041 Uiso 1 calc
C5 C 0.40179(17) 0.5905(4) 0.1708(2) 0.0332(9) Uani 1 d
H5 H 0.4428 0.6214 0.2194 0.04 Uiso 1 calc
C6 C 0.37069(16) 0.6614(3) 0.0961(2) 0.0313(9) Uani 1 d
H6 H 0.3903 0.7407 0.0928 0.038 Uiso 1 calc
C7 C 0.31073(16) 0.6168(3) 0.0259(2) 0.0265(9) Uani 1 d
C8 C 0.27626(16) 0.6050(3) -0.1090(2) 0.0273(9) Uani 1 d
C9 C 0.31235(16) 0.6404(3) -0.1344(2) 0.0284(9) Uani 1 d
H9 H 0.3405 0.7182 -0.11 0.034 Uiso 1 calc
C10 C 0.30749(17) 0.5624(3) -0.1954(2) 0.0354(10) Uani 1 d
H10 H 0.3322 0.5861 -0.213 0.043 Uiso 1 calc
C11 C 0.26603(18) 0.4491(3) -0.2305(2) 0.0379(11) Uani 1 d
H11 H 0.2625 0.3946 -0.2721 0.046 Uiso 1 calc
C12 C 0.22978(17) 0.4152(3) -0.2051(2) 0.0333(10) Uani 1 d
H12 H 0.2009 0.3388 -0.2308 0.04 Uiso 1 calc
C13 C 0.23465(15) 0.4906(3) -0.1428(2) 0.0272(9) Uani 1 d
C14 C 0.17079(16) 0.4841(3) 0.0316(2) 0.0299(9) Uani 1 d
H14A H 0.14 0.5624 0.0037 0.036 Uiso 1 calc
H14B H 0.2139 0.5222 0.0778 0.036 Uiso 1 calc
C15 C 0.14942(15) 0.3857(3) 0.0679(2) 0.0309(9) Uani 1 d
H15A H 0.1815 0.3102 0.0988 0.037 Uiso 1 calc
H15B H 0.147 0.436 0.1082 0.037 Uiso 1 calc
C16 C 0.08744(17) 0.2602(3) -0.0657(2) 0.0346(10) Uani 1 d
H16A H 0.1168 0.1791 -0.0403 0.042 Uiso 1 calc
H16B H 0.0438 0.2264 -0.1131 0.042 Uiso 1 calc
C17 C 0.11049(16) 0.3586(3) -0.0989(2) 0.0349(10) Uani 1 d
H17A H 0.1134 0.3097 -0.1392 0.042 Uiso 1 calc
H17B H 0.0792 0.4357 -0.1291 0.042 Uiso 1 calc
C18 C 0.06180(17) 0.2181(3) 0.0291(2) 0.0323(10) Uani 1 d
H18A H 0.0959 0.1464 0.06 0.039 Uiso 1 calc
H18B H 0.0233 0.1727 -0.0216 0.039 Uiso 1 calc
C19 C 0.04418(16) 0.2607(3) 0.0848(2) 0.0318(10) Uani 1 d
C20 C -0.01067(17) 0.3697(3) 0.0413(2) 0.0311(9) Uani 1 d
C21 C 0.10129(16) 0.3062(3) 0.1739(2) 0.0389(10) Uani 1 d
H21A H 0.1126 0.4024 0.1728 0.058 Uiso 1 calc
H21B H 0.1385 0.2461 0.1955 0.058 Uiso 1 calc
H21C H 0.0894 0.2992 0.2107 0.058 Uiso 1 calc
C22 C 0.01416(17) 0.1288(3) 0.0913(2) 0.0400(10) Uani 1 d
H22A H 0.0012 0.1484 0.1262 0.06 Uiso 1 calc
H22B H 0.0461 0.0538 0.117 0.06 Uiso 1 calc
H22C H -0.0238 0.1007 0.0348 0.06 Uiso 1 calc
O1 O 0.28010(10) 0.6889(2) -0.04992(13) 0.0281(6) Uani 1 d
O2 O -0.01218(11) 0.4510(2) 0.08853(15) 0.0408(7) Uani 1 d
O3 O -0.05171(11) 0.3679(2) -0.03712(16) 0.0404(7) Uani 1 d
N1 N 0.19447(13) 0.4543(2) -0.12269(18) 0.0296(8) Uani 1 d
N2 N 0.17401(13) 0.4138(3) -0.02936(17) 0.0298(8) Uani 1 d
N3 N 0.08481(13) 0.3254(3) -0.00077(18) 0.0294(8) Uani 1 d
H1 H 0.0555(17) 0.396(3) -0.030(2) 0.042(10) Uiso 1 d
O4A O 0.0772(2) 0.7107(6) 0.1884(4) 0.0486(19) Uani 0.683(11) d
H41A H 0.060(3) 0.688(6) 0.1392(16) 0.073 Uiso 0.683(11) d
H42A H 0.090(4) 0.646(5) 0.221(3) 0.073 Uiso 0.683(11) d
O4B O 0.0759(5) 0.7823(13) 0.1647(6) 0.031(3) Uani 0.298(6) d
H41B H 0.072(6) 0.749(12) 0.124(5) 0.046 Uiso 0.298(6) d
H42B H 0.100(7) 0.739(12) 0.208(4) 0.046 Uiso 0.298(6) d
O5 O 0.0571(3) 0.5575(7) 0.2363(4) 0.028(3) Uani 0.298(6) d
H51 H 0.094(2) 0.539(10) 0.278(4) 0.042 Uiso 0.298(6) d
H52 H 0.045(4) 0.513(10) 0.194(3) 0.042 Uiso 0.298(6) d
O6 O 0.0035(8) 0.3569(5) 0.2347(7) 0.047(4) Uani 0.453(6) d
H61 H -0.006(5) 0.366(5) 0.187(3) 0.07 Uiso 0.453(6) d
H62 H 0 0.433(2) 0.25 0.07 Uiso 0.453(6) 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
N1 C1 N2 118.9(3)
N1 C1 C2 125.2(4)
N2 C1 C2 115.6(3)
C7 C2 C3 118.2(3)
C7 C2 C1 120.5(3)
C3 C2 C1 121.3(3)
C4 C3 C2 120.9(3)
C3 C4 C5 119.6(3)
C6 C5 C4 120.3(3)
C5 C6 C7 119.6(3)
C6 C7 C2 121.3(3)
C6 C7 O1 119.0(3)
C2 C7 O1 119.7(3)
C9 C8 O1 118.8(3)
C9 C8 C13 121.8(3)
O1 C8 C13 119.4(3)
C8 C9 C10 120.1(3)
C9 C10 C11 119.2(4)
C12 C11 C10 120.3(4)
C11 C12 C13 121.6(3)
C12 C13 C8 117.1(4)
C12 C13 N1 118.6(3)
C8 C13 N1 124.1(3)
N2 C14 C15 111.2(3)
N3 C15 C14 110.4(3)
C17 C16 N3 112.7(3)
N2 C17 C16 110.0(3)
N3 C18 C19 120.1(3)
C18 C19 C21 115.0(3)
C18 C19 C20 111.9(3)
C21 C19 C20 111.2(3)
C18 C19 C22 104.7(3)
C21 C19 C22 108.3(3)
C20 C19 C22 105.0(3)
O3 C20 O2 124.4(3)
O3 C20 C19 118.5(3)
O2 C20 C19 117.0(3)
C7 O1 C8 109.9(2)
C1 N1 C13 122.0(3)
C1 N2 C14 121.1(3)
C1 N2 C17 118.8(3)
C14 N2 C17 110.3(3)
C15 N3 C16 109.2(3)
C15 N3 C18 114.0(3)
C16 N3 C18 108.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.304(4) .
C1 N2 1.378(4) .
C1 C2 1.494(4) .
C2 C7 1.388(5) .
C2 C3 1.398(4) .
C3 C4 1.379(5) .
C4 C5 1.393(5) .
C5 C6 1.375(5) .
C6 C7 1.383(4) .
C7 O1 1.398(4) .
C8 C9 1.384(5) .
C8 O1 1.399(4) .
C8 C13 1.399(5) .
C9 C10 1.386(5) .
C10 C11 1.389(5) .
C11 C12 1.383(5) .
C12 C13 1.396(5) .
C13 N1 1.403(4) .
C14 N2 1.462(4) .
C14 C15 1.513(5) .
C15 N3 1.493(4) .
C16 C17 1.499(5) .
C16 N3 1.503(4) .
C17 N2 1.463(4) .
C18 N3 1.509(4) .
C18 C19 1.528(5) .
C19 C21 1.529(5) .
C19 C20 1.547(5) .
C19 C22 1.550(5) .
C20 O3 1.248(4) .
C20 O2 1.260(4) .
O4A O4B 0.829(9) .
O6 O6 0.752(14) 2
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 44.1(5)
N2 C1 C2 C7 -142.4(3)
N1 C1 C2 C3 -136.4(4)
N2 C1 C2 C3 37.2(4)
C7 C2 C3 C4 2.2(5)
C1 C2 C3 C4 -177.4(3)
C2 C3 C4 C5 -0.2(5)
C3 C4 C5 C6 -1.3(5)
C4 C5 C6 C7 0.7(5)
C5 C6 C7 C2 1.4(5)
C5 C6 C7 O1 -179.2(3)
C3 C2 C7 C6 -2.8(5)
C1 C2 C7 C6 176.7(3)
C3 C2 C7 O1 177.7(3)
C1 C2 C7 O1 -2.7(5)
O1 C8 C9 C10 -177.4(3)
C13 C8 C9 C10 0.5(5)
C8 C9 C10 C11 0.1(5)
C9 C10 C11 C12 0.4(5)
C10 C11 C12 C13 -1.5(5)
C11 C12 C13 C8 2.1(4)
C11 C12 C13 N1 177.3(3)
C9 C8 C13 C12 -1.6(4)
O1 C8 C13 C12 176.3(3)
C9 C8 C13 N1 -176.5(3)
O1 C8 C13 N1 1.4(4)
N2 C14 C15 N3 -58.4(3)
N3 C16 C17 N2 56.7(4)
N3 C18 C19 C21 -69.0(4)
N3 C18 C19 C20 59.1(4)
N3 C18 C19 C22 172.3(3)
C18 C19 C20 O3 30.3(4)
C21 C19 C20 O3 160.5(3)
C22 C19 C20 O3 -82.6(4)
C18 C19 C20 O2 -152.6(3)
C21 C19 C20 O2 -22.5(4)
C22 C19 C20 O2 94.4(3)
C6 C7 O1 C8 113.1(3)
C2 C7 O1 C8 -67.5(4)
C9 C8 O1 C7 -112.1(3)
C13 C8 O1 C7 69.9(3)
N2 C1 N1 C13 -175.0(3)
C2 C1 N1 C13 -1.7(5)
C12 C13 N1 C1 143.9(3)
C8 C13 N1 C1 -41.2(4)
N1 C1 N2 C14 -143.0(3)
C2 C1 N2 C14 43.1(4)
N1 C1 N2 C17 -0.4(4)
C2 C1 N2 C17 -174.4(3)
C15 C14 N2 C1 -154.6(3)
C15 C14 N2 C17 60.0(3)
C16 C17 N2 C1 155.4(3)
C16 C17 N2 C14 -58.3(3)
C14 C15 N3 C16 54.2(3)
C14 C15 N3 C18 175.8(3)
C17 C16 N3 C15 -54.6(4)
C17 C16 N3 C18 -179.5(3)
C19 C18 N3 C15 67.8(4)
C19 C18 N3 C16 -170.3(3)
