#------------------------------------------------------------------------------
#$Date: 2015-12-09 13:12:36 +0200 (Wed, 09 Dec 2015) $
#$Revision: 170938 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/93/1529300.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_1529300
loop_
_publ_author_name
'Weiss, Ryan J.'
'Gordts, Philip L. S. M.'
'Le, Dzung'
'Xu, Ding'
'Esko, Jeffrey D.'
'Tor, Yitzhak'
_publ_section_title
;
 Small molecule antagonists of cell-surface heparan sulfate and
 heparin--protein interactions
;
_journal_issue                   10
_journal_name_full               'Chem. Sci.'
_journal_page_first              5984
_journal_paper_doi               10.1039/C5SC01208B
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C13 H14 N3 O2'
_chemical_formula_weight         244.27
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.595(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5132(5)
_cell_length_b                   21.0477(13)
_cell_length_c                   7.2003(4)
_cell_measurement_reflns_used    9705
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.61
_cell_volume                     1182.31(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20966
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.611
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       rod
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0650P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2209
_reflns_number_total             2413
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5sc01208b2.cif
_cod_data_source_block           tor86
_cod_depositor_comments
'Adding full bibliography for 1529300--1529303.cif.'
_cod_database_code               1529300
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1S O -0.05291(15) 0.39864(6) 1.10342(19) 0.0212(3) Uani 1 1 d . .
O1 O -0.14002(15) 0.44074(6) 0.41328(17) 0.0214(3) Uani 1 1 d . .
N1 N 0.65814(17) 0.34047(6) 0.8202(2) 0.0170(3) Uani 1 1 d . .
N2 N 0.01848(17) 0.43140(7) 0.7538(2) 0.0168(3) Uani 1 1 d . .
H2 H 0.0121 0.4358 0.8722 0.020 Uiso 1 1 calc R U
N3 N 0.23188(19) 0.30567(7) 0.2734(2) 0.0247(4) Uani 1 1 d . .
C1 C 0.8462(2) 0.28284(8) 0.7007(3) 0.0218(4) Uani 1 1 d . .
H1 H 0.8798 0.3000 0.5954 0.033 Uiso 1 1 calc R U
H7 H 0.8423 0.2364 0.6925 0.033 Uiso 1 1 calc R U
H8 H 0.9299 0.2959 0.8343 0.033 Uiso 1 1 calc R U
C2 C 0.6719(2) 0.30787(7) 0.6700(3) 0.0171(3) Uani 1 1 d . .
C3 C 0.4972(2) 0.36109(7) 0.7943(2) 0.0161(3) Uani 1 1 d . .
C4 C 0.4791(2) 0.39412(8) 0.9563(2) 0.0193(4) Uani 1 1 d . .
H11 H 0.5768 0.4009 1.0788 0.023 Uiso 1 1 calc R U
C5 C 0.3226(2) 0.41634(8) 0.9381(2) 0.0189(4) Uani 1 1 d . .
H12 H 0.3132 0.4387 1.0477 0.023 Uiso 1 1 calc R U
C6 C 0.1743(2) 0.40646(8) 0.7578(2) 0.0164(3) Uani 1 1 d . .
C7 C -0.1220(2) 0.44927(7) 0.5899(2) 0.0159(3) Uani 1 1 d . .
C8 C -0.25617(19) 0.48348(7) 0.6411(2) 0.0158(3) Uani 1 1 d . .
H4 H -0.2201 0.5282 0.6750 0.019 Uiso 1 1 calc R U
H3 H -0.2618 0.4636 0.7628 0.019 Uiso 1 1 calc R U
C9 C -0.43452(19) 0.48246(7) 0.4703(2) 0.0157(3) Uani 1 1 d . .
H5 H -0.4717 0.4379 0.4361 0.019 Uiso 1 1 calc R U
H6 H -0.4301 0.5027 0.3483 0.019 Uiso 1 1 calc R U
C10 C 0.1872(2) 0.37320(7) 0.6008(2) 0.0163(3) Uani 1 1 d . .
H10 H 0.0874 0.3652 0.4817 0.020 Uiso 1 1 calc R U
C11 C 0.3485(2) 0.35076(7) 0.6147(2) 0.0154(3) Uani 1 1 d . .
C12 C 0.5321(2) 0.29559(8) 0.4856(3) 0.0190(4) Uani 1 1 d . .
H9 H 0.5497 0.2722 0.3827 0.023 Uiso 1 1 calc R U
C13 C 0.3693(2) 0.31707(8) 0.4522(3) 0.0175(4) Uani 1 1 d . .
H1X H -0.149(4) 0.3769(13) 1.024(4) 0.047(7) Uiso 1 1 d . .
H1Y H -0.078(3) 0.4146(13) 1.197(4) 0.041(7) 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
_geom_angle_site_symmetry_3
C2 N1 C3 117.45(14) .
C7 N2 C6 127.85(14) .
N1 C2 C12 123.17(15) .
N1 C2 C1 117.73(14) .
C12 C2 C1 119.10(15) .
N1 C3 C4 118.22(14) .
N1 C3 C11 123.50(15) .
C4 C3 C11 118.28(14) .
C5 C4 C3 120.74(15) .
C4 C5 C6 120.93(15) .
C10 C6 N2 123.80(15) .
C10 C6 C5 119.57(15) .
N2 C6 C5 116.62(14) .
O1 C7 N2 124.13(14) .
O1 C7 C8 121.71(14) .
N2 C7 C8 114.13(13) .
C7 C8 C9 113.71(13) .
C8 C9 C9 111.67(16) 3_466
C6 C10 C11 120.46(15) .
C10 C11 C3 119.98(14) .
C10 C11 C13 122.53(14) .
C3 C11 C13 117.49(14) .
C13 C12 C2 120.95(15) .
N3 C13 C12 121.68(15) .
N3 C13 C11 120.92(14) .
C12 C13 C11 117.39(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.232(2) .
N1 C2 1.325(2) .
N1 C3 1.377(2) .
N2 C7 1.354(2) .
N2 C6 1.416(2) .
N3 C13 1.370(2) .
C1 C2 1.505(2) .
C2 C12 1.407(2) .
C3 C4 1.418(2) .
C3 C11 1.418(2) .
C4 C5 1.368(2) .
C5 C6 1.418(2) .
C6 C10 1.371(2) .
C7 C8 1.515(2) .
C8 C9 1.524(2) .
C9 C9 1.533(3) 3_466
C10 C11 1.417(2) .
C11 C13 1.439(2) .
C12 C13 1.384(2) .
