#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/33/2103304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2103304
loop_
_publ_author_name
'Cole, Jacqueline M.'
'Goeta, Andrés E.'
'Howard, Judith A. K.'
'McIntyre, Garry J.'
_publ_section_title
;
 X-ray and neutron diffraction studies of the non-linear optical
 compounds MBANP and MBADNP at 20K: charge-density and hydrogen-bonding
 analyses
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              690
_journal_page_last               700
_journal_paper_doi               10.1107/S0108768102006109
_journal_volume                  58
_journal_year                    2002
_chemical_formula_sum            'C13 H13 N3 O2'
_chemical_formula_weight         243.00
_chemical_name_common            'methylbenzylaminonitropyridine (MBANP)'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3210(10)
_cell_length_b                   6.2930(10)
_cell_length_c                   17.650(4)
_cell_measurement_reflns_used    4
_cell_measurement_temperature    20.00(10)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     589.8(2)
_computing_cell_refinement       'RAFD9 (local program)'
_computing_data_collection       'MAD (Barthelemy, 1984)'
_computing_data_reduction        'RACER (Wilkinson et al, 1988)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1995)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      20.00(10)
_diffrn_measurement_device
'The high-flux four-circle diffractometer, D9'
_diffrn_measurement_method       'ω-x-θ scans'
_diffrn_radiation_monochromator  'Cu (220)'
_diffrn_radiation_probe          neutron
_diffrn_radiation_source
'Institut Laue Langevin Reactor, Grenoble, France'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.83717
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4116
_diffrn_reflns_theta_max         46.46
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.1582
_exptl_absorpt_correction_T_max  0.8574
_exptl_absorpt_correction_T_min  0.7263
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Gaussian integration (Coppens et al, 1965)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    none
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             182
_exptl_crystal_size_max          4.3
_exptl_crystal_size_mid          2.0
_exptl_crystal_size_min          1.0
_refine_diff_density_max         1.795
_refine_diff_density_min         -1.868
_refine_ls_abs_structure_details
;
Absolute structure known a priori from reagents in synthesis
(see paper)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   2.557
_refine_ls_goodness_of_fit_obs   2.632
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.679
_refine_ls_restrained_S_obs      2.631
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_obs          0.0732
_refine_ls_shift/esd_max         -0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1111
_refine_ls_wR_factor_obs         0.1051
_reflns_number_observed          2619
_reflns_number_total             2805
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            an0602.cif
_cod_data_source_block           MBANP
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               2103304
_cod_database_fobs_code          2103304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O1 0.6458(6) 0.1528(5) 0.4698(2) 0.0103(5) Uani d 1 O
O2 0.3175(6) 0.1837(5) 0.3915(2) 0.0114(5) Uani d 1 O
N1 0.8817(3) 0.9896(3) 0.30042(12) 0.0080(3) Uani d 1 N
H1N 1.0504(10) 1.0463(11) 0.3223(4) 0.0223(13) Uani d 1 H
N2 0.5712(3) 0.7316(3) 0.30259(12) 0.0081(3) Uani d 1 N
N3 0.5221(3) 0.2486(3) 0.41967(12) 0.0075(3) Uani d 1 N
C1 0.8083(4) 0.9335(4) 0.1617(2) 0.0069(4) Uani d 1 C
C2 0.6266(4) 0.9362(4) 0.1012(2) 0.0084(4) Uani d 1 C
H2 0.4594(11) 1.0339(11) 0.1057(5) 0.0248(13) Uani d 1 H
C3 0.6576(5) 0.8155(4) 0.0366(2) 0.0093(4) Uani d 1 C
H3 0.5144(13) 0.8191(12) -0.0089(4) 0.0238(13) Uani d 1 H
C4 0.8723(5) 0.6900(4) 0.0317(2) 0.0086(4) Uani d 1 C
H4 0.8973(13) 0.5943(12) -0.0180(4) 0.0241(13) Uani d 1 H
C5 1.0539(4) 0.6858(4) 0.0915(2) 0.0082(4) Uani d 1 C
H5 1.2218(11) 0.5898(12) 0.0879(4) 0.0241(13) Uani d 1 H
C6 1.0243(4) 0.8075(4) 0.1567(2) 0.0080(4) Uani d 1 C
H6 1.1690(11) 0.8058(12) 0.2031(4) 0.0219(12) Uani d 1 H
C7 0.7761(4) 1.0788(4) 0.2293(2) 0.0067(4) Uani d 1 C
H7 0.5722(9) 1.1041(10) 0.2343(4) 0.0177(10) Uani d 1 H
C8 0.9068(5) 1.2913(4) 0.2160(2) 0.0101(4) Uani d 1 C
H8A 0.8927(15) 1.3966(11) 0.2642(5) 0.0282(14) Uani d 1 H
H8B 0.8215(14) 1.3687(13) 0.1664(5) 0.030(2) Uani d 1 H
H8C 1.1034(13) 1.2654(12) 0.2071(5) 0.0286(15) Uani d 1 H
C9 0.7922(4) 0.8116(4) 0.3324(2) 0.0068(4) Uani d 1 C
C10 0.9319(4) 0.7158(4) 0.3944(2) 0.0078(4) Uani d 1 C
H10 1.1051(11) 0.7868(11) 0.4161(4) 0.0226(12) Uani d 1 H
C11 0.8457(4) 0.5305(4) 0.4240(2) 0.0075(4) Uani d 1 C
H11 0.9485(12) 0.4492(12) 0.4702(4) 0.0235(12) Uani d 1 H
C12 0.6180(4) 0.4461(4) 0.3917(2) 0.0071(4) Uani d 1 C
C13 0.4876(4) 0.5519(4) 0.3326(2) 0.0075(4) Uani d 1 C
H13 0.3098(11) 0.4870(12) 0.3092(4) 0.0221(12) Uani d 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
C9 N1 C7 123.4(2)
C9 N1 H1N 117.2(4)
C7 N1 H1N 118.3(4)
C13 N2 C9 117.6(2)
O1 N3 O2 123.1(3)
O1 N3 C12 119.0(2)
O2 N3 C12 117.9(2)
C2 C1 C6 119.3(2)
C2 C1 C7 119.1(2)
C6 C1 C7 121.4(2)
C3 C2 C1 120.6(2)
C3 C2 H2 120.7(5)
C1 C2 H2 118.7(5)
C2 C3 C4 120.0(2)
C2 C3 H3 119.2(4)
C4 C3 H3 120.8(5)
C5 C4 C3 119.9(3)
C5 C4 H4 119.5(4)
C3 C4 H4 120.6(4)
C4 C5 C6 120.4(2)
C4 C5 H5 120.2(5)
C6 C5 H5 119.4(5)
C5 C6 C1 119.7(2)
C5 C6 H6 120.2(4)
C1 C6 H6 120.1(4)
N1 C7 C1 112.9(2)
N1 C7 C8 108.3(2)
C1 C7 C8 109.2(2)
N1 C7 H7 108.3(4)
C1 C7 H7 108.0(4)
C8 C7 H7 110.1(4)
C7 C8 H8A 111.0(5)
C7 C8 H8B 110.3(5)
H8A C8 H8B 108.3(7)
C7 C8 H8C 110.1(4)
H8A C8 H8C 108.8(6)
H8B C8 H8C 108.2(7)
N2 C9 N1 117.8(2)
N2 C9 C10 122.8(2)
N1 C9 C10 119.5(2)
C11 C10 C9 119.0(2)
C11 C10 H10 121.3(5)
C9 C10 H10 119.7(4)
C10 C11 C12 117.9(2)
C10 C11 H11 121.7(4)
C12 C11 H11 120.4(4)
C13 C12 C11 120.0(2)
C13 C12 N3 120.0(2)
C11 C12 N3 120.0(2)
N2 C13 C12 122.8(2)
N2 C13 H13 118.1(4)
C12 C13 H13 119.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.226(4)
O2 N3 1.237(3)
N1 C9 1.354(3)
N1 C7 1.455(3)
N1 H1N 1.019(5)
N2 C13 1.337(3)
N2 C9 1.354(3)
N3 C12 1.443(3)
C1 C2 1.394(4)
C1 C6 1.404(3)
C1 C7 1.522(4)
C2 C3 1.388(4)
C2 H2 1.089(6)
C3 C4 1.396(4)
C3 H3 1.072(8)
C4 C5 1.385(4)
C4 H4 1.080(7)
C5 C6 1.399(4)
C5 H5 1.084(6)
C6 H6 1.087(6)
C7 C8 1.532(4)
C7 H7 1.106(6)
C8 H8A 1.085(8)
C8 H8B 1.076(8)
C8 H8C 1.080(7)
C9 C10 1.418(4)
C10 C11 1.369(4)
C10 H10 1.073(7)
C11 C12 1.409(3)
C11 H11 1.082(7)
C12 C13 1.386(4)
C13 H13 1.088(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188378
