#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/36/4503627.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_4503627
loop_
_publ_author_name
'Hauser, Melanie R.'
'Zhakarov, Lev'
'Doxsee, Kenneth M.'
'Li, Tonglei'
_publ_section_title
;
 Polymorphism of a Simple Organic Amide
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4428
_journal_paper_doi               10.1021/cg800171h
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_name_systematic
; 
 ? 
;
_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                 94.4750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7611(3)
_cell_length_b                   12.2633(6)
_cell_length_c                   10.3091(5)
_cell_measurement_reflns_used    3524
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.59
_cell_volume                     726.12(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6150
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.2493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                1598
_reflns_number_total             1716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800171h_si_001.cif
_cod_data_source_block           mrh12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4503627
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
O1 O 1.04046(14) 0.44341(7) 0.13175(8) 0.0249(2) Uani 1 1 d
O2 O 0.47872(14) 0.49290(7) 0.24513(8) 0.0263(2) Uani 1 1 d
N1 N 0.69304(15) 0.58612(7) 0.10233(9) 0.0200(2) Uani 1 1 d
C1 C 0.84755(18) 0.41999(9) 0.20355(11) 0.0217(2) Uani 1 1 d
C2 C 0.65387(18) 0.50411(8) 0.18486(10) 0.0192(2) Uani 1 1 d
C3 C 0.54875(18) 0.67706(8) 0.06876(10) 0.0194(2) Uani 1 1 d
C4 C 0.34440(19) 0.69961(9) 0.12802(11) 0.0238(3) Uani 1 1 d
C5 C 0.2132(2) 0.79107(10) 0.08981(12) 0.0271(3) Uani 1 1 d
C6 C 0.2828(2) 0.86056(10) -0.00548(12) 0.0292(3) Uani 1 1 d
C7 C 0.4871(2) 0.83869(10) -0.06329(12) 0.0286(3) Uani 1 1 d
C8 C 0.6207(2) 0.74763(9) -0.02696(10) 0.0232(2) Uani 1 1 d
H1 H 1.158(3) 0.4574(14) 0.1825(17) 0.043(5) Uiso 1 1 d
H1A H 0.779(3) 0.3494(12) 0.1748(15) 0.031(4) Uiso 1 1 d
H1B H 0.888(2) 0.4169(12) 0.2979(15) 0.027(3) Uiso 1 1 d
H2 H 0.825(3) 0.5777(12) 0.0592(15) 0.031(4) Uiso 1 1 d
H4 H 0.299(3) 0.6521(12) 0.1940(15) 0.031(4) Uiso 1 1 d
H5 H 0.074(3) 0.8060(13) 0.1341(14) 0.031(4) Uiso 1 1 d
H6 H 0.192(3) 0.9218(13) -0.0307(16) 0.038(4) Uiso 1 1 d
H7 H 0.539(3) 0.8872(14) -0.1293(17) 0.040(4) Uiso 1 1 d
H8 H 0.762(3) 0.7325(12) -0.0671(15) 0.030(4) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0178(4) 0.0319(4) 0.0252(4) 0.0023(3) 0.0018(3) 0.0030(3)
O2 0.0189(4) 0.0316(5) 0.0288(4) 0.0062(3) 0.0050(3) -0.0019(3)
N1 0.0168(4) 0.0213(5) 0.0222(4) 0.0015(3) 0.0036(3) 0.0019(3)
C1 0.0195(5) 0.0218(5) 0.0236(5) 0.0030(4) 0.0006(4) -0.0001(4)
C2 0.0175(5) 0.0209(5) 0.0186(5) -0.0013(4) -0.0014(4) -0.0023(4)
C3 0.0183(5) 0.0191(5) 0.0203(5) -0.0025(4) -0.0010(4) 0.0004(4)
C4 0.0203(5) 0.0231(5) 0.0286(6) -0.0028(4) 0.0048(4) -0.0011(4)
C5 0.0195(5) 0.0276(6) 0.0341(6) -0.0089(5) 0.0013(4) 0.0032(4)
C6 0.0303(6) 0.0255(6) 0.0307(6) -0.0031(5) -0.0052(5) 0.0096(5)
C7 0.0360(6) 0.0254(6) 0.0243(6) 0.0029(4) 0.0015(5) 0.0057(5)
C8 0.0239(5) 0.0236(5) 0.0222(5) -0.0001(4) 0.0029(4) 0.0027(4)
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
C1 O1 H1 110.1(12)
C2 N1 C3 128.12(9)
C2 N1 H2 114.1(10)
C3 N1 H2 117.6(10)
O1 C1 C2 113.29(9)
O1 C1 H1A 109.5(9)
C2 C1 H1A 106.5(9)
O1 C1 H1B 112.9(8)
C2 C1 H1B 105.5(8)
H1A C1 H1B 108.8(12)
O2 C2 N1 125.82(10)
O2 C2 C1 118.79(9)
N1 C2 C1 115.39(9)
C4 C3 C8 119.50(10)
C4 C3 N1 123.20(10)
C8 C3 N1 117.28(9)
C5 C4 C3 119.58(11)
C5 C4 H4 121.5(9)
C3 C4 H4 118.9(9)
C6 C5 C4 121.08(11)
C6 C5 H5 120.9(9)
C4 C5 H5 118.0(9)
C5 C6 C7 119.27(11)
C5 C6 H6 120.1(10)
C7 C6 H6 120.6(10)
C6 C7 C8 120.67(11)
C6 C7 H7 120.3(10)
C8 C7 H7 119.1(10)
C7 C8 C3 119.89(11)
C7 C8 H8 120.6(9)
C3 C8 H8 119.5(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4121(13)
O1 H1 0.841(19)
O2 C2 1.2333(13)
N1 C2 1.3477(14)
N1 C3 1.4176(13)
N1 H2 0.915(16)
C1 C2 1.5208(15)
C1 H1A 0.988(15)
C1 H1B 0.983(15)
C3 C4 1.3957(15)
C3 C8 1.3994(15)
C4 C5 1.3921(16)
C4 H4 0.948(16)
C5 C6 1.3834(18)
C5 H5 0.971(15)
C6 C7 1.3863(18)
C6 H6 0.941(17)
C7 C8 1.3907(16)
C7 H7 0.970(17)
C8 H8 0.961(15)
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 O2 0.841(19) 1.958(19) 2.7656(12) 160.8(16) 1_655
N1 H2 O1 0.915(16) 2.161(15) 2.6582(12) 113.2(12) .
N1 H2 O1 0.915(16) 2.187(16) 2.9817(12) 144.8(13) 3_765
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 232186
