#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/35/4123590.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_4123590
loop_
_publ_author_name
'Sigala, Paul A.'
'Ruben, Eliza A.'
'Liu, Corey W.'
'Piccoli, Paula M. B.'
'Hohenstein, Edward G.'
'Martínez, Todd J'
'Schultz, Arthur J.'
'Herschlag, Daniel'
_publ_section_title
;
 Determination of Hydrogen Bond Structure in Water versus Aprotic
 Environments To Test the Relationship Between Length and Stability.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5730
_journal_page_last               5740
_journal_paper_doi               10.1021/ja512980h
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C21 H22 N4 O7'
_chemical_formula_weight         442.43
_chemical_melting_point          'C21 H22 N4 O7'
_chemical_name_systematic
;
 3,5-dinitrosalicylate N,N,N',N'-tetramethyl-1,8-napthalenediamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.3890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9407(5)
_cell_length_b                   13.6994(7)
_cell_length_c                   15.9341(8)
_cell_measurement_temperature    293(2)
_cell_volume                     2119.40(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20979
_diffrn_reflns_theta_full        24.41
_diffrn_reflns_theta_max         24.41
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.812193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0026(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          1.397
_refine_ls_shift/su_mean         0.045
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.7590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                2510
_reflns_number_total             3487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            980682.cif
_cod_data_source_block           paulo
_cod_depositor_comments
'Adding full bibliography for 4123587--4123590.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4123590
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C2A C -0.0451(3) 0.8185(3) 0.1718(2) 0.0956(11) Uani 1 1 d .
H2A1 H -0.0949 0.8675 0.1346 0.143 Uiso 1 1 calc R
H2A2 H -0.0251 0.8421 0.2299 0.143 Uiso 1 1 calc R
H2A3 H -0.0997 0.7603 0.1683 0.143 Uiso 1 1 calc R
C2B C 0.1663(4) 0.7220(2) 0.2002(2) 0.1028(11) Uani 1 1 d .
H2B1 H 0.1790 0.7413 0.2593 0.154 Uiso 1 1 calc R
H2B2 H 0.2545 0.7152 0.1854 0.154 Uiso 1 1 calc R
H2B3 H 0.1185 0.6607 0.1919 0.154 Uiso 1 1 calc R
H1 H 0.171(3) 0.882(2) 0.143(2) 0.100(10) Uiso 1 1 d .
H10 H -0.109(5) 1.272(4) 0.413(4) 0.22(2) Uiso 1 1 d .
N1 N 0.23470(19) 0.94234(14) 0.11860(12) 0.0519(5) Uani 1 1 d .
N2 N 0.0852(2) 0.79659(15) 0.14519(12) 0.0595(5) Uani 1 1 d .
C14 C 0.1929(2) 1.07560(18) 0.58370(15) 0.0569(6) Uani 1 1 d .
O5 O 0.2896(2) 1.08432(18) 0.72774(12) 0.0913(7) Uani 1 1 d .
C1 C 0.2233(2) 0.90772(16) 0.03055(14) 0.0487(5) Uani 1 1 d .
10 C 0.1360(2) 0.82724(16) 0.00229(14) 0.0484(5) Uiso 1 1 d .
C11 C 0.0235(3) 1.15135(18) 0.43333(16) 0.0588(6) Uani 1 1 d .
C16 C 0.0245(2) 1.19047(17) 0.51639(16) 0.0559(6) Uani 1 1 d .
C12 C 0.1101(2) 1.06862(17) 0.43264(14) 0.0543(6) Uani 1 1 d .
O1 O -0.0468(3) 1.18852(18) 0.36472(13) 0.1036(8) Uani 1 1 d .
C5 C 0.1160(3) 0.8013(2) -0.08653(16) 0.0623(7) Uani 1 1 d .
C13 C 0.1941(2) 1.03262(18) 0.50571(15) 0.0582(6) Uani 1 1 d .
H13 H 0.2514 0.9796 0.5027 0.070 Uiso 1 1 calc R
N3 N 0.2844(3) 1.0399(2) 0.66067(15) 0.0749(7) Uani 1 1 d .
N4 N 0.1113(3) 1.01950(19) 0.35092(16) 0.0785(7) Uani 1 1 d .
C15 C 0.1079(2) 1.15397(18) 0.58899(16) 0.0574(6) Uani 1 1 d .
H15 H 0.1074 1.1820 0.6421 0.069 Uiso 1 1 calc R
O2 O 0.0142(3) 1.0325(2) 0.29038(14) 0.1176(9) Uani 1 1 d .
C9 C 0.0645(2) 0.77213(18) 0.05429(16) 0.0590(6) Uani 1 1 d .
O6 O -0.0759(3) 1.30388(19) 0.59424(18) 0.1138(9) Uani 1 1 d .
O4 O 0.3548(3) 0.9685(2) 0.65587(15) 0.1140(9) Uani 1 1 d .
O3 O 0.2028(3) 0.9655(2) 0.34430(14) 0.1260(11) Uani 1 1 d .
C2 C 0.2888(3) 0.9559(2) -0.02339(18) 0.0698(7) Uani 1 1 d .
H2 H 0.3460 1.0083 -0.0031 0.084 Uiso 1 1 calc R
C1B C 0.1637(3) 1.03739(19) 0.12011(19) 0.0733(8) Uani 1 1 d .
H1B1 H 0.1721 1.0582 0.1785 0.110 Uiso 1 1 calc R
H1B2 H 0.0680 1.0303 0.0933 0.110 Uiso 1 1 calc R
H1B3 H 0.2050 1.0852 0.0894 0.110 Uiso 1 1 calc R
O7 O -0.1286(3) 1.3152(2) 0.4556(2) 0.1240(10) Uani 1 1 d .
C4 C 0.1864(3) 0.8529(3) -0.13966(17) 0.0779(9) Uani 1 1 d .
H4 H 0.1746 0.8355 -0.1972 0.094 Uiso 1 1 calc R
C17 C -0.0642(3) 1.2735(2) 0.5258(2) 0.0702(7) Uani 1 1 d .
C1A C 0.3788(3) 0.9459(3) 0.16852(18) 0.0812(9) Uani 1 1 d .
H1A1 H 0.3800 0.9690 0.2256 0.122 Uiso 1 1 calc R
H1A2 H 0.4315 0.9894 0.1408 0.122 Uiso 1 1 calc R
H1A3 H 0.4182 0.8817 0.1715 0.122 Uiso 1 1 calc R
C8 C -0.0210(3) 0.6985(3) 0.0199(2) 0.0973(11) Uani 1 1 d .
H8 H -0.0667 0.6624 0.0546 0.117 Uiso 1 1 calc R
C7 C -0.0408(4) 0.6765(3) -0.0678(3) 0.1169(14) Uani 1 1 d .
H7 H -0.1012 0.6267 -0.0909 0.140 Uiso 1 1 calc R
C3 C 0.2711(3) 0.9275(3) -0.1089(2) 0.0838(9) Uani 1 1 d .
H3 H 0.3180 0.9603 -0.1450 0.101 Uiso 1 1 calc R
C6 C 0.0259(3) 0.7259(3) -0.1185(2) 0.0916(10) Uani 1 1 d .
H6 H 0.0118 0.7096 -0.1764 0.110 Uiso 1 1 calc R
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
N2 C2A H2A1 109.5
N2 C2A H2A2 109.5
H2A1 C2A H2A2 109.5
N2 C2A H2A3 109.5
H2A1 C2A H2A3 109.5
H2A2 C2A H2A3 109.5
N2 C2B H2B1 109.5
N2 C2B H2B2 109.5
H2B1 C2B H2B2 109.5
N2 C2B H2B3 109.5
H2B1 C2B H2B3 109.5
H2B2 C2B H2B3 109.5
C1 N1 C1A 113.13(19)
C1 N1 C1B 111.16(19)
C1A N1 C1B 111.7(2)
C1 N1 H1 98.5(15)
C1A N1 H1 112.4(15)
C1B N1 H1 109.2(15)
C9 N2 C2B 112.1(2)
C9 N2 C2A 112.7(2)
C2B N2 C2A 111.9(3)
C9 N2 H1 96.6(12)
C2B N2 H1 109.0(12)
C2A N2 H1 113.7(12)
C13 C14 C15 120.8(2)
C13 C14 N3 119.7(2)
C15 C14 N3 119.6(2)
C2 C1 10 121.5(2)
C2 C1 N1 120.1(2)
10 C1 N1 118.29(19)
C1 10 C9 125.3(2)
C1 10 C5 117.0(2)
C9 10 C5 117.7(2)
O1 C11 C12 122.3(2)
O1 C11 C16 122.7(2)
C12 C11 C16 115.0(2)
C15 C16 C11 122.1(2)
C15 C16 C17 117.8(2)
C11 C16 C17 120.1(2)
C13 C12 C11 122.6(2)
C13 C12 N4 118.0(2)
C11 C12 N4 119.4(2)
C11 O1 H10 93.9(19)
C6 C5 C4 121.3(3)
C6 C5 10 119.3(3)
C4 C5 10 119.4(2)
C12 C13 C14 119.4(2)
C12 C13 H13 120.3
C14 C13 H13 120.3
O4 N3 O5 122.6(2)
O4 N3 C14 119.0(2)
O5 N3 C14 118.3(3)
O3 N4 O2 120.5(3)
O3 N4 C12 120.9(2)
O2 N4 C12 118.5(2)
C16 C15 C14 120.1(2)
C16 C15 H15 120.0
C14 C15 H15 119.9
C8 C9 10 120.5(2)
C8 C9 N2 121.0(2)
10 C9 N2 118.4(2)
C1 C2 C3 120.5(3)
C1 C2 H2 119.8
C3 C2 H2 119.7
N1 C1B H1B1 109.5
N1 C1B H1B2 109.5
H1B1 C1B H1B2 109.5
N1 C1B H1B3 109.5
H1B1 C1B H1B3 109.5
H1B2 C1B H1B3 109.5
C17 O7 H10 101(3)
C3 C4 C5 121.1(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
O6 C17 O7 120.4(3)
O6 C17 C16 122.8(3)
O7 C17 C16 116.7(3)
N1 C1A H1A1 109.5
N1 C1A H1A2 109.5
H1A1 C1A H1A2 109.5
N1 C1A H1A3 109.5
H1A1 C1A H1A3 109.5
H1A2 C1A H1A3 109.5
C9 C8 C7 120.3(3)
C9 C8 H8 119.8
C7 C8 H8 119.8
C6 C7 C8 120.9(3)
C6 C7 H7 119.6
C8 C7 H7 119.6
C4 C3 C2 120.4(3)
C4 C3 H3 119.8
C2 C3 H3 119.8
C7 C6 C5 121.3(3)
C7 C6 H6 119.4
C5 C6 H6 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2A N2 1.478(3)
C2A H2A1 0.9600
C2A H2A2 0.9600
C2A H2A3 0.9600
C2B N2 1.470(4)
C2B H2B1 0.9600
C2B H2B2 0.9600
C2B H2B3 0.9600
N1 C1 1.462(3)
N1 C1A 1.483(3)
N1 C1B 1.484(3)
N1 H1 1.16(3)
N2 C9 1.458(3)
N2 H1 1.45(3)
C14 C13 1.377(3)
C14 C15 1.380(3)
C14 N3 1.446(3)
O5 N3 1.221(3)
C1 C2 1.356(3)
C1 10 1.415(3)
10 C9 1.419(3)
10 C5 1.431(3)
C11 O1 1.271(3)
C11 C12 1.425(3)
C11 C16 1.426(3)
C16 C15 1.365(3)
C16 C17 1.466(4)
C12 C13 1.371(3)
C12 N4 1.468(3)
O1 H10 1.58(6)
C5 C6 1.390(4)
C5 C4 1.401(4)
C13 H13 0.9300
N3 O4 1.215(3)
N4 O3 1.194(3)
N4 O2 1.223(3)
C15 H15 0.9300
C9 C8 1.357(4)
O6 C17 1.196(3)
C2 C3 1.391(4)
C2 H2 0.9300
C1B H1B1 0.9600
C1B H1B2 0.9600
C1B H1B3 0.9600
O7 C17 1.297(4)
O7 H10 0.95(6)
C4 C3 1.348(4)
C4 H4 0.9300
C1A H1A1 0.9600
C1A H1A2 0.9600
C1A H1A3 0.9600
C8 C7 1.400(5)
C8 H8 0.9300
C7 C6 1.335(5)
C7 H7 0.9300
C3 H3 0.9300
C6 H6 0.9300
