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#$Date: 2017-02-03 22:21:28 +0200 (Fri, 03 Feb 2017) $
#$Revision: 191234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/40/4514019.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_4514019
loop_
_publ_author_name
'Cisneros, José A'
'Robertson, Michael J.'
'Mercado, Brandon Q.'
'Jorgensen, William L.'
_publ_section_title
;
 Systematic Study of Effects of Structural Modifications on the Aqueous
 Solubility of Drug-like Molecules.
;
_journal_issue                   1
_journal_name_full               'ACS medicinal chemistry letters'
_journal_page_first              124
_journal_page_last               127
_journal_paper_doi               10.1021/acsmedchemlett.6b00451
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C17 H12 N4 O'
_chemical_formula_sum            'C17 H12 N4 O'
_chemical_formula_weight         288.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.608(4)
_cell_length_b                   4.4122(5)
_cell_length_c                   10.4910(11)
_cell_measurement_reflns_used    5668
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.3390
_cell_measurement_theta_min      3.0470
_cell_volume                     1324.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_molecular_graphics
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2503
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            44130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.547
_diffrn_reflns_theta_max         66.547
_diffrn_reflns_theta_min         3.090
_diffrn_source                   'Rigaku Saturn 944+ CCD'
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
; 
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_coef       0.0046(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0860
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1111P)²+3.2939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2092
_refine_ls_wR_factor_ref         0.2421
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1685
_reflns_number_total             2348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ml6b00451_si_002.cif
_cod_data_source_block           007-16010
_cod_database_code               4514019
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.5426(2) 1.1364(16) 0.9264(6) 0.0402(17) Uani 1 1 d . .
H1 H 0.572(5) 1.07(3) 0.879(13) 0.07(4) Uiso 1 1 d . .
N1 N 0.3984(3) 0.5214(18) 0.6837(8) 0.0380(18) Uani 1 1 d . .
N2 N 0.3575(3) 0.469(2) 0.7471(8) 0.040(2) Uani 1 1 d . .
N3 N 0.3312(3) 0.2946(19) 0.6739(8) 0.041(2) Uani 1 1 d . .
N4 N 0.3655(3) -0.0430(19) 0.3692(8) 0.0390(19) Uani 1 1 d . .
C1 C 0.3986(3) 0.375(2) 0.5697(10) 0.039(2) Uani 1 1 d . .
H1A H 0.4227 0.3730 0.5075 0.047 Uiso 1 1 calc R U
C2 C 0.3558(3) 0.229(2) 0.5643(9) 0.036(2) Uani 1 1 d . .
C3 C 0.3362(3) 0.037(2) 0.4629(8) 0.037(2) Uani 1 1 d . .
C4 C 0.2898(3) -0.062(2) 0.4694(9) 0.039(2) Uani 1 1 d . .
H4 H 0.2705 -0.0064 0.5393 0.047 Uiso 1 1 calc R U
C5 C 0.2727(3) -0.241(2) 0.3732(9) 0.041(2) Uani 1 1 d . .
H5 H 0.2410 -0.3054 0.3744 0.049 Uiso 1 1 calc R U
C6 C 0.3023(3) -0.328(2) 0.2729(10) 0.038(2) Uani 1 1 d . .
C7 C 0.2872(3) -0.517(2) 0.1700(10) 0.041(2) Uani 1 1 d . .
H7 H 0.2558 -0.5861 0.1674 0.049 Uiso 1 1 calc R U
C8 C 0.3175(3) -0.599(2) 0.0756(10) 0.043(2) Uani 1 1 d . .
H8 H 0.3074 -0.7305 0.0092 0.051 Uiso 1 1 calc R U
C9 C 0.3636(3) -0.489(2) 0.0769(9) 0.038(2) Uani 1 1 d . .
H9 H 0.3843 -0.5436 0.0098 0.045 Uiso 1 1 calc R U
C10 C 0.3793(3) -0.306(2) 0.1730(9) 0.038(2) Uani 1 1 d . .
H10 H 0.4106 -0.2345 0.1726 0.046 Uiso 1 1 calc R U
C11 C 0.3485(3) -0.221(2) 0.2736(9) 0.032(2) Uani 1 1 d . .
C12 C 0.4355(3) 0.683(2) 0.7419(9) 0.035(2) Uani 1 1 d . .
C13 C 0.4261(3) 0.891(2) 0.8392(9) 0.038(2) Uani 1 1 d . .
H13 H 0.3948 0.9314 0.8633 0.046 Uiso 1 1 calc R U
C14 C 0.4623(3) 1.036(2) 0.9003(9) 0.038(2) Uani 1 1 d . .
H14 H 0.4557 1.1753 0.9671 0.046 Uiso 1 1 calc R U
C15 C 0.5084(3) 0.981(2) 0.8647(9) 0.036(2) Uani 1 1 d . .
C16 C 0.5175(3) 0.775(2) 0.7676(9) 0.037(2) Uani 1 1 d . .
H16 H 0.5488 0.7384 0.7414 0.045 Uiso 1 1 calc R U
C17 C 0.4809(3) 0.622(2) 0.7090(9) 0.039(2) Uani 1 1 d . .
H17 H 0.4874 0.4749 0.6455 0.047 Uiso 1 1 calc R U
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 O1 H1 102(7)
C1 N1 N2 110.5(8)
C1 N1 C12 128.1(8)
N2 N1 C12 121.1(8)
N3 N2 N1 107.7(7)
N2 N3 C2 108.5(8)
C3 N4 C11 117.8(8)
N1 C1 C2 104.8(8)
N1 C1 H1A 127.6
C2 C1 H1A 127.6
N3 C2 C1 108.5(8)
N3 C2 C3 122.0(8)
C1 C2 C3 129.4(9)
N4 C3 C4 123.3(8)
N4 C3 C2 116.3(8)
C4 C3 C2 120.4(8)
C5 C4 C3 118.8(9)
C5 C4 H4 120.6
C3 C4 H4 120.6
C4 C5 C6 119.6(9)
C4 C5 H5 120.2
C6 C5 H5 120.2
C11 C6 C5 118.2(9)
C11 C6 C7 119.0(9)
C5 C6 C7 122.8(9)
C8 C7 C6 120.7(9)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 119.8(10)
C7 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C8 121.2(9)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 119.9(9)
C9 C10 H10 120.0
C11 C10 H10 120.0
N4 C11 C6 122.3(8)
N4 C11 C10 118.3(8)
C6 C11 C10 119.3(8)
C17 C12 C13 119.5(9)
C17 C12 N1 120.1(9)
C13 C12 N1 120.2(8)
C14 C13 C12 120.2(9)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 120.4(9)
C13 C14 H14 119.8
C15 C14 H14 119.8
O1 C15 C16 123.1(9)
O1 C15 C14 117.8(9)
C16 C15 C14 119.2(9)
C17 C16 C15 120.1(9)
C17 C16 H16 120.0
C15 C16 H16 120.0
C12 C17 C16 120.6(9)
C12 C17 H17 119.7
C16 C17 H17 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.358(12)
O1 H1 1.01(14)
N1 C1 1.360(13)
N1 N2 1.367(11)
N1 C12 1.416(12)
N2 N3 1.321(11)
N3 C2 1.380(13)
N4 C3 1.339(12)
N4 C11 1.365(12)
C1 C2 1.383(14)
C1 H1A 0.9500
C2 C3 1.471(13)
C3 C4 1.400(13)
C4 C5 1.371(14)
C4 H4 0.9500
C5 C6 1.405(13)
C5 H5 0.9500
C6 C11 1.402(13)
C6 C7 1.431(14)
C7 C8 1.365(14)
C7 H7 0.9500
C8 C9 1.406(14)
C8 H8 0.9500
C9 C10 1.369(14)
C9 H9 0.9500
C10 C11 1.424(13)
C10 H10 0.9500
C12 C17 1.371(13)
C12 C13 1.397(14)
C13 C14 1.375(14)
C13 H13 0.9500
C14 C15 1.393(13)
C14 H14 0.9500
C15 C16 1.389(14)
C16 C17 1.388(13)
C16 H16 0.9500
C17 H17 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N4 1.01(14) 1.81(13) 2.727(11) 150(11) 2_665
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
C1 N1 N2 N3 -1.2(10)
C12 N1 N2 N3 -175.2(8)
N1 N2 N3 C2 1.6(10)
N2 N1 C1 C2 0.2(10)
C12 N1 C1 C2 173.8(9)
N2 N3 C2 C1 -1.5(11)
N2 N3 C2 C3 179.7(9)
N1 C1 C2 N3 0.7(11)
N1 C1 C2 C3 179.5(9)
C11 N4 C3 C4 2.3(13)
C11 N4 C3 C2 180.0(8)
N3 C2 C3 N4 -171.6(9)
C1 C2 C3 N4 9.8(15)
N3 C2 C3 C4 6.1(14)
C1 C2 C3 C4 -172.5(10)
N4 C3 C4 C5 -2.4(15)
C2 C3 C4 C5 -179.9(10)
C3 C4 C5 C6 1.9(15)
C4 C5 C6 C11 -1.6(14)
C4 C5 C6 C7 179.2(10)
C11 C6 C7 C8 1.8(15)
C5 C6 C7 C8 -179.1(10)
C6 C7 C8 C9 -2.1(16)
C7 C8 C9 C10 1.5(16)
C8 C9 C10 C11 -0.4(14)
C3 N4 C11 C6 -1.9(13)
C3 N4 C11 C10 179.6(9)
C5 C6 C11 N4 1.6(14)
C7 C6 C11 N4 -179.2(9)
C5 C6 C11 C10 -179.9(9)
C7 C6 C11 C10 -0.7(13)
C9 C10 C11 N4 178.6(9)
C9 C10 C11 C6 0.1(13)
C1 N1 C12 C17 -22.8(14)
N2 N1 C12 C17 150.1(9)
C1 N1 C12 C13 161.5(9)
N2 N1 C12 C13 -25.6(13)
C17 C12 C13 C14 0.9(15)
N1 C12 C13 C14 176.7(9)
C12 C13 C14 C15 0.8(15)
C13 C14 C15 O1 178.5(9)
C13 C14 C15 C16 -0.6(14)
O1 C15 C16 C17 179.7(9)
C14 C15 C16 C17 -1.3(14)
C13 C12 C17 C16 -2.8(15)
N1 C12 C17 C16 -178.5(9)
C15 C16 C17 C12 3.0(14)
