#------------------------------------------------------------------------------
#$Date: 2017-06-05 03:19:15 +0300 (Mon, 05 Jun 2017) $
#$Revision: 197414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/60/4126022.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_4126022
loop_
_publ_author_name
'Maier, Josef M.'
'Li, Ping'
'Vik, Erik C.'
'Yehl, Christopher J.'
'Strickland, Sharon M. S.'
'Shimizu, Ken D.'
_publ_section_title
;
 Measurement of Solvent OH-π Interactions Using a Molecular Balance.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6550
_journal_page_last               6553
_journal_paper_doi               10.1021/jacs.7b02349
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.419(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5608(8)
_cell_length_b                   6.4181(5)
_cell_length_c                   19.8406(14)
_cell_measurement_reflns_used    9706
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.669
_cell_measurement_theta_min      2.178
_cell_volume                     1344.77(17)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.631 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18020
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.712
_diffrn_reflns_theta_min         2.053
_diffrn_source_current           38.0
_diffrn_source_power             1.786
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0455
_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)+(0.0731P)²+0.0981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                2510
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b02349_si_002.cif
_cod_data_source_block           lpc217m
_cod_depositor_comments          'Adding full bibliography for 4126022.cif.'
_cod_database_code               4126022
_shelxl_version_number           2014-3
_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.
;
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
1.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C15(H15)
1.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.65602(10) 0.68950(16) 0.71249(5) 0.0232(3) Uani 1 1 d .
O2 O 0.24662(9) 0.55514(17) 0.77010(5) 0.0238(3) Uani 1 1 d .
O3 O 0.36058(11) 0.11921(18) 0.44909(5) 0.0294(3) Uani 1 1 d .
O4 O 0.30745(10) 0.44338(17) 0.41822(5) 0.0243(3) Uani 1 1 d .
N1 N 0.44280(11) 0.62114(18) 0.72552(6) 0.0173(3) Uani 1 1 d .
C1 C 0.53837(14) 0.7071(2) 0.93327(7) 0.0233(3) Uani 1 1 d .
H1A H 0.5286 0.8585 0.9412 0.026(4) Uiso 1 1 calc R
H1B H 0.5666 0.6365 0.9751 0.024(4) Uiso 1 1 calc R
C2 C 0.62318(14) 0.6577(2) 0.87270(7) 0.0213(3) Uani 1 1 d .
H2 H 0.7149 0.6939 0.8778 0.022(4) Uiso 1 1 calc R
C3 C 0.54747(14) 0.7801(2) 0.81694(7) 0.0196(3) Uani 1 1 d .
H3 H 0.5681 0.9321 0.8184 0.025(4) Uiso 1 1 calc R
C4 C 0.56014(14) 0.6952(2) 0.74629(7) 0.0181(3) Uani 1 1 d .
C5 C 0.35065(13) 0.6305(2) 0.77617(7) 0.0183(3) Uani 1 1 d .
C6 C 0.40770(14) 0.7414(2) 0.83620(7) 0.0187(3) Uani 1 1 d .
H6 H 0.3628 0.8755 0.8453 0.028(4) Uiso 1 1 calc R
C7 C 0.41894(14) 0.6064(2) 0.90167(7) 0.0202(3) Uani 1 1 d .
H7 H 0.3422 0.6007 0.9308 0.023(4) Uiso 1 1 calc R
C8 C 0.47319(14) 0.3980(2) 0.87956(7) 0.0223(3) Uani 1 1 d .
H8 H 0.4295 0.2687 0.8785 0.024(4) Uiso 1 1 calc R
C9 C 0.59281(14) 0.4298(2) 0.86207(7) 0.0227(3) Uani 1 1 d .
H9 H 0.6495 0.3270 0.8457 0.030(5) Uiso 1 1 calc R
C10 C 0.41717(13) 0.5365(2) 0.65939(7) 0.0169(3) Uani 1 1 d .
C11 C 0.45644(13) 0.3356(2) 0.64320(7) 0.0181(3) Uani 1 1 d .
C12 C 0.42771(13) 0.2640(2) 0.57859(7) 0.0193(3) Uani 1 1 d .
H12 H 0.4520 0.1270 0.5660 0.021(4) Uiso 1 1 calc R
C13 C 0.36420(13) 0.3890(2) 0.53223(7) 0.0186(3) Uani 1 1 d .
C14 C 0.32752(13) 0.5899(2) 0.54936(7) 0.0202(3) Uani 1 1 d .
H14 H 0.2853 0.6758 0.5173 0.023(4) Uiso 1 1 calc R
C15 C 0.35324(13) 0.6636(2) 0.61373(7) 0.0187(3) Uani 1 1 d .
H15 H 0.3274 0.7997 0.6265 0.012(4) Uiso 1 1 calc R
C16 C 0.52951(14) 0.2036(2) 0.69219(7) 0.0223(3) Uani 1 1 d .
H16A H 0.6075 0.2759 0.7054 0.032(5) Uiso 1 1 calc GR
H16B H 0.5508 0.0703 0.6710 0.037(5) Uiso 1 1 calc GR
H16C H 0.4780 0.1781 0.7322 0.030(5) Uiso 1 1 calc GR
C17 C 0.34399(13) 0.3000(2) 0.46309(7) 0.0208(3) Uani 1 1 d .
H4 H 0.310(2) 0.390(4) 0.3772(13) 0.065(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 O4 H4 109.6(15)
C4 N1 C5 113.24(11)
C4 N1 C10 124.06(11)
C5 N1 C10 122.67(11)
H1A C1 H1B 110.3
C2 C1 H1A 112.9
C2 C1 H1B 112.9
C2 C1 C7 94.31(11)
C7 C1 H1A 112.9
C7 C1 H1B 112.9
C1 C2 H2 116.3
C1 C2 C3 98.69(11)
C3 C2 H2 116.3
C9 C2 C1 100.62(12)
C9 C2 H2 116.3
C9 C2 C3 106.22(11)
C2 C3 H3 111.0
C4 C3 C2 115.15(12)
C4 C3 H3 111.0
C4 C3 C6 105.20(11)
C6 C3 C2 103.13(11)
C6 C3 H3 111.0
O1 C4 N1 124.75(12)
O1 C4 C3 126.92(13)
N1 C4 C3 108.32(12)
O2 C5 N1 123.13(13)
O2 C5 C6 128.78(13)
N1 C5 C6 108.06(12)
C3 C6 H6 111.1
C3 C6 C7 103.14(11)
C5 C6 C3 104.89(11)
C5 C6 H6 111.1
C5 C6 C7 114.94(12)
C7 C6 H6 111.1
C1 C7 C6 99.33(11)
C1 C7 H7 116.3
C6 C7 H7 116.3
C8 C7 C1 100.17(12)
C8 C7 C6 105.89(11)
C8 C7 H7 116.3
C7 C8 H8 126.2
C9 C8 C7 107.53(14)
C9 C8 H8 126.2
C2 C9 H9 125.9
C8 C9 C2 108.26(13)
C8 C9 H9 125.9
C11 C10 N1 120.26(12)
C15 C10 N1 117.27(12)
C15 C10 C11 122.48(13)
C10 C11 C12 117.02(13)
C10 C11 C16 121.77(13)
C12 C11 C16 121.19(13)
C11 C12 H12 119.4
C13 C12 C11 121.30(13)
C13 C12 H12 119.4
C12 C13 C17 116.76(13)
C14 C13 C12 120.55(13)
C14 C13 C17 122.62(13)
C13 C14 H14 120.4
C15 C14 C13 119.25(13)
C15 C14 H14 120.4
C10 C15 H15 120.3
C14 C15 C10 119.39(13)
C14 C15 H15 120.3
C11 C16 H16A 109.5
C11 C16 H16B 109.5
C11 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O3 C17 O4 123.45(13)
O3 C17 C13 123.85(13)
O4 C17 C13 112.69(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.2191(17)
O2 C5 1.2058(17)
O3 C17 1.2060(19)
O4 C17 1.3355(18)
O4 H4 0.88(3)
N1 C4 1.3871(18)
N1 C5 1.4054(19)
N1 C10 1.4438(17)
C1 H1A 0.9900
C1 H1B 0.9900
C1 C2 1.537(2)
C1 C7 1.546(2)
C2 H2 1.0000
C2 C3 1.5708(19)
C2 C9 1.512(2)
C3 H3 1.0000
C3 C4 1.5108(19)
C3 C6 1.548(2)
C5 C6 1.5089(19)
C6 H6 1.0000
C6 C7 1.5649(19)
C7 H7 1.0000
C7 C8 1.521(2)
C8 H8 0.9500
C8 C9 1.328(2)
C9 H9 0.9500
C10 C11 1.393(2)
C10 C15 1.3905(19)
C11 C12 1.3931(19)
C11 C16 1.499(2)
C12 H12 0.9500
C12 C13 1.389(2)
C13 C14 1.389(2)
C13 C17 1.4999(19)
C14 H14 0.9500
C14 C15 1.387(2)
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
O4 H4 O1 0.88(3) 1.89(3) 2.7597(15) 169(2) 3_666
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
O2 C5 C6 C3 173.80(14)
O2 C5 C6 C7 61.28(19)
N1 C5 C6 C3 -4.40(15)
N1 C5 C6 C7 -116.93(13)
N1 C10 C11 C12 179.64(12)
N1 C10 C11 C16 -2.0(2)
N1 C10 C15 C14 179.38(12)
C1 C2 C3 C4 -152.21(13)
C1 C2 C3 C6 -38.20(13)
C1 C2 C9 C8 32.05(15)
C1 C7 C8 C9 -33.12(14)
C2 C1 C7 C6 -59.05(12)
C2 C1 C7 C8 49.09(12)
C2 C3 C4 O1 -65.21(19)
C2 C3 C4 N1 114.27(13)
C2 C3 C6 C5 -119.26(12)
C2 C3 C6 C7 1.41(14)
C3 C2 C9 C8 -70.34(15)
C3 C6 C7 C1 35.66(13)
C3 C6 C7 C8 -67.80(13)
C4 N1 C5 O2 -172.56(13)
C4 N1 C5 C6 5.77(16)
C4 N1 C10 C11 76.81(18)
C4 N1 C10 C15 -102.89(16)
C4 C3 C6 C5 1.77(14)
C4 C3 C6 C7 122.44(11)
C5 N1 C4 O1 174.93(13)
C5 N1 C4 C3 -4.57(16)
C5 N1 C10 C11 -101.23(16)
C5 N1 C10 C15 79.07(17)
C5 C6 C7 C1 149.21(12)
C5 C6 C7 C8 45.75(16)
C6 C3 C4 O1 -178.01(14)
C6 C3 C4 N1 1.47(15)
C6 C7 C8 C9 69.72(14)
C7 C1 C2 C3 59.68(12)
C7 C1 C2 C9 -48.75(12)
C7 C8 C9 C2 0.81(15)
C9 C2 C3 C4 -48.40(16)
C9 C2 C3 C6 65.60(14)
C10 N1 C4 O1 -3.3(2)
C10 N1 C4 C3 177.22(12)
C10 N1 C5 O2 5.7(2)
C10 N1 C5 C6 -176.00(12)
C10 C11 C12 C13 0.8(2)
C11 C10 C15 C14 -0.3(2)
C11 C12 C13 C14 0.0(2)
C11 C12 C13 C17 177.02(12)
C12 C13 C14 C15 -1.0(2)
C12 C13 C17 O3 12.4(2)
C12 C13 C17 O4 -166.58(12)
C13 C14 C15 C10 1.2(2)
C14 C13 C17 O3 -170.61(14)
C14 C13 C17 O4 10.40(19)
C15 C10 C11 C12 -0.7(2)
C15 C10 C11 C16 177.67(13)
C16 C11 C12 C13 -177.52(13)
C17 C13 C14 C15 -177.86(13)
