#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:18:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179571 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/36/4503628.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_4503628
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            'C16 H18 N2 O4'
_chemical_formula_weight         302.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.167(3)
_cell_length_b                   5.6343(13)
_cell_length_c                   18.694(5)
_cell_measurement_reflns_used    3251
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.61
_cell_volume                     1492.2(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 0.961
_diffrn_measured_fraction_theta_max 0.961
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9127
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0389
_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)+(0.0641P)²+0.3015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                1538
_reflns_number_total             1780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800171h_si_002.cif
_cod_data_source_block           mrh15a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_cell_volume        1492.1(6)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4503628
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.57072(6) 0.50371(15) 0.56740(5) 0.0333(2) Uani 1 1 d
O2 O 0.67195(6) -0.07747(14) 0.55521(5) 0.0346(2) Uani 1 1 d
N1 N 0.60071(7) 0.15996(16) 0.47172(5) 0.0239(2) Uani 1 1 d
C1 C 0.61367(9) 0.2960(2) 0.59404(6) 0.0283(3) Uani 1 1 d
C2 C 0.63186(8) 0.10778(19) 0.53773(6) 0.0247(3) Uani 1 1 d
C3 C 0.61026(7) 0.02683(19) 0.40775(6) 0.0224(3) Uani 1 1 d
C4 C 0.57206(8) 0.12659(19) 0.34593(6) 0.0263(3) Uani 1 1 d
C5 C 0.58184(8) 0.0125(2) 0.28078(7) 0.0305(3) Uani 1 1 d
C6 C 0.62942(8) -0.2024(2) 0.27622(7) 0.0308(3) Uani 1 1 d
C7 C 0.66587(8) -0.3025(2) 0.33766(7) 0.0287(3) Uani 1 1 d
C8 C 0.65674(8) -0.19124(19) 0.40379(6) 0.0260(3) Uani 1 1 d
H1 H 0.6116(13) 0.612(3) 0.5643(10) 0.056(5) Uiso 1 1 d
H1A H 0.5702(10) 0.224(3) 0.6300(7) 0.034(4) Uiso 1 1 d
H1B H 0.6733(10) 0.331(3) 0.6175(8) 0.036(4) Uiso 1 1 d
H2 H 0.5711(10) 0.296(3) 0.4680(7) 0.030(4) Uiso 1 1 d
H4 H 0.5390(10) 0.276(3) 0.3493(7) 0.031(3) Uiso 1 1 d
H5 H 0.5541(10) 0.079(3) 0.2396(8) 0.035(4) Uiso 1 1 d
H6 H 0.6379(10) -0.278(3) 0.2293(8) 0.037(4) Uiso 1 1 d
H7 H 0.6973(10) -0.451(2) 0.3354(7) 0.028(3) Uiso 1 1 d
H8 H 0.6839(9) -0.259(2) 0.4455(7) 0.030(3) 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 0.0321(5) 0.0237(4) 0.0440(5) -0.0047(4) 0.0038(4) 0.0030(4)
O2 0.0443(5) 0.0230(4) 0.0364(5) 0.0015(3) -0.0100(4) 0.0050(4)
N1 0.0252(5) 0.0184(4) 0.0280(5) 0.0004(3) 0.0006(4) 0.0037(4)
C1 0.0293(6) 0.0249(6) 0.0305(6) -0.0006(4) 0.0030(5) -0.0024(4)
C2 0.0232(5) 0.0207(5) 0.0303(6) 0.0008(4) 0.0011(4) -0.0028(4)
C3 0.0193(5) 0.0200(5) 0.0279(6) 0.0002(4) 0.0019(4) -0.0020(4)
C4 0.0241(5) 0.0224(5) 0.0323(6) 0.0028(4) 0.0011(4) 0.0023(4)
C5 0.0300(6) 0.0326(6) 0.0288(6) 0.0016(5) -0.0026(5) 0.0007(5)
C6 0.0282(6) 0.0316(6) 0.0324(6) -0.0081(5) -0.0002(5) -0.0021(5)
C7 0.0244(5) 0.0211(5) 0.0407(7) -0.0053(4) -0.0001(5) 0.0003(4)
C8 0.0242(5) 0.0208(5) 0.0329(6) 0.0010(4) -0.0018(4) 0.0008(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 109.2(12)
C2 N1 C3 128.88(10)
C2 N1 H2 114.9(9)
C3 N1 H2 116.2(9)
O1 C1 C2 114.12(10)
O1 C1 H1A 107.9(8)
C2 C1 H1A 106.9(9)
O1 C1 H1B 111.5(9)
C2 C1 H1B 107.9(9)
H1A C1 H1B 108.3(12)
O2 C2 N1 125.48(11)
O2 C2 C1 119.12(11)
N1 C2 C1 115.40(10)
C4 C3 C8 119.59(10)
C4 C3 N1 116.66(10)
C8 C3 N1 123.73(10)
C5 C4 C3 120.22(10)
C5 C4 H4 120.7(8)
C3 C4 H4 119.1(8)
C4 C5 C6 120.49(11)
C4 C5 H5 119.5(9)
C6 C5 H5 120.0(9)
C7 C6 C5 119.15(11)
C7 C6 H6 121.2(9)
C5 C6 H6 119.6(9)
C6 C7 C8 121.35(11)
C6 C7 H7 120.0(8)
C8 C7 H7 118.7(8)
C7 C8 C3 119.17(11)
C7 C8 H8 120.7(8)
C3 C8 H8 120.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4099(15)
O1 H1 0.842(19)
O2 C2 1.2324(14)
N1 C2 1.3430(15)
N1 C3 1.4181(14)
N1 H2 0.879(15)
C1 C2 1.5162(16)
C1 H1A 0.997(14)
C1 H1B 0.972(15)
C3 C4 1.3944(16)
C3 C8 1.3959(15)
C4 C5 1.3840(17)
C4 H4 0.964(14)
C5 C6 1.3886(17)
C5 H5 0.942(15)
C6 C7 1.3798(18)
C6 H6 0.983(15)
C7 C8 1.3921(17)
C7 H7 0.947(14)
C8 H8 0.949(14)
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 0.842(19) 1.956(19) 2.7707(13) 162.5(17) 1_565
N1 H2 O1 0.879(15) 2.194(14) 2.6703(13) 113.6(11) .
N1 H2 O1 0.879(15) 2.396(15) 3.1661(14) 146.5(12) 5_666
