#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/35/4123589.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_4123589
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_moiety         'C12 H12 N2 O5'
_chemical_formula_sum            'C12 H12 N2 O5'
_chemical_formula_weight         264.24
_chemical_name_systematic
; 
 4-nitrophenol 4-methoxypyridine-N-oxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-11-06 # Formatted by publCIF
;
_cell_angle_alpha                87.7810(10)
_cell_angle_beta                 80.5520(10)
_cell_angle_gamma                70.1870(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6545(4)
_cell_length_b                   6.7300(4)
_cell_length_c                   14.5060(9)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      33.07
_cell_measurement_theta_min      2.85
_cell_volume                     602.80(6)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10936
_diffrn_reflns_theta_full        33.55
_diffrn_reflns_theta_max         33.55
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.765348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.000(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          4.482
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0868P)²+0.0606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                3303
_reflns_number_total             4453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            978286.cif
_cod_data_source_block           pbar
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4123587--4123590.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4123589
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.66554(18) 0.3191(2) 0.10121(8) 0.0515(4) Uani 1 1 d
N2 N 0.88518(14) 0.72780(13) 0.61208(6) 0.02376(18) Uani 1 1 d
C1 C 0.94814(16) 0.75341(15) 0.52054(7) 0.02395(19) Uani 1 1 d
H1 H 1.089(2) 0.758(2) 0.5078(11) 0.033(4) Uiso 1 1 d
O1 O 0.5840(2) 0.2062(3) 0.15193(8) 0.0712(4) Uani 1 1 d
O2 O 0.6828(2) 0.4813(3) 0.12884(9) 0.0736(4) Uani 1 1 d
O3 O 0.98604(15) 0.07696(15) -0.26958(5) 0.0344(2) Uani 1 1 d
H13 H 0.995(3) -0.060(4) -0.2849(15) 0.070(6) Uiso 1 1 d
O4 O 1.01953(13) 0.71363(13) 0.67363(6) 0.03308(19) Uani 1 1 d
O5 O 0.46997(12) 0.75028(13) 0.42853(6) 0.02908(18) Uani 1 1 d
C2 C 0.81663(16) 0.76072(15) 0.45569(7) 0.02327(19) Uani 1 1 d
H2 H 0.868(2) 0.768(2) 0.3930(11) 0.034(4) Uiso 1 1 d
C3 C 0.61278(15) 0.74354(14) 0.48536(7) 0.02220(19) Uani 1 1 d
C4 C 0.54956(16) 0.71962(16) 0.58070(7) 0.0257(2) Uani 1 1 d
H4 H 0.411(2) 0.709(2) 0.6016(10) 0.032(3) Uiso 1 1 d
C5 C 0.68794(17) 0.71052(17) 0.64217(7) 0.0265(2) Uani 1 1 d
H5 H 0.654(2) 0.692(2) 0.7091(10) 0.032(4) Uiso 1 1 d
C6 C 0.5453(2) 0.7399(2) 0.32891(8) 0.0327(2) Uani 1 1 d
H6C H 0.671(2) 0.609(2) 0.3113(10) 0.027(3) Uiso 1 1 d
H6B H 0.583(3) 0.864(3) 0.3087(11) 0.039(4) Uiso 1 1 d
H6A H 0.428(3) 0.727(3) 0.3023(12) 0.047(4) Uiso 1 1 d
C7 C 0.74488(17) 0.2553(2) 0.00382(7) 0.0346(3) Uani 1 1 d
C8 C 0.82541(19) 0.3864(2) -0.05581(9) 0.0353(3) Uani 1 1 d
H8 H 0.829(3) 0.514(3) -0.0340(11) 0.041(4) Uiso 1 1 d
C9 C 0.90573(19) 0.32422(19) -0.14790(8) 0.0319(2) Uani 1 1 d
H9 H 0.965(3) 0.417(3) -0.1897(13) 0.047(4) Uiso 1 1 d
C10 C 0.90560(17) 0.13033(17) -0.17979(7) 0.0260(2) Uani 1 1 d
C11 C 0.82269(18) 0.00045(19) -0.11851(8) 0.0293(2) Uani 1 1 d
H11 H 0.825(3) -0.137(3) -0.1431(12) 0.044(4) Uiso 1 1 d
C12 C 0.74283(18) 0.0630(2) -0.02635(8) 0.0337(3) Uani 1 1 d
H12 H 0.691(3) -0.024(3) 0.0196(12) 0.052(5) 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
O2 N1 O1 123.36(13)
O2 N1 C7 118.71(14)
O1 N1 C7 117.93(14)
O4 N2 C1 120.23(8)
O4 N2 C5 119.61(9)
C1 N2 C5 120.14(9)
N2 C1 C2 121.35(9)
C3 O5 C6 117.53(8)
C1 C2 C3 119.34(9)
O5 C3 C2 124.59(9)
O5 C3 C4 117.00(9)
C2 C3 C4 118.41(9)
C5 C4 C3 119.87(9)
N2 C5 C4 120.88(9)
C12 C7 C8 121.96(10)
C12 C7 N1 119.15(12)
C8 C7 N1 118.88(13)
C9 C8 C7 119.12(11)
C8 C9 C10 119.85(11)
O3 C10 C9 117.51(9)
O3 C10 C11 122.34(10)
C9 C10 C11 120.15(10)
C12 C11 C10 119.85(11)
C11 C12 C7 119.08(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.225(2)
N1 O1 1.232(2)
N1 C7 1.4517(15)
N2 O4 1.3428(11)
N2 C1 1.3480(13)
N2 C5 1.3558(13)
C1 C2 1.3751(14)
O3 C10 1.3375(12)
O5 C3 1.3454(12)
O5 C6 1.4459(14)
C2 C3 1.3962(14)
C3 C4 1.3976(14)
C4 C5 1.3688(15)
C7 C12 1.3868(19)
C7 C8 1.3872(19)
C8 C9 1.3793(17)
C9 C10 1.4016(15)
C10 C11 1.4015(15)
C11 C12 1.3804(16)
