#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:28:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179665 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/18/4511822.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_4511822
loop_
_publ_author_name
'Nauha, Elisa'
'Bernstein, Joel'
_publ_section_title
;
 “Predicting” Crystal Forms of Pharmaceuticals Using
 Hydrogen Bond Propensities: Two Test Cases
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4364
_journal_paper_doi               10.1021/cg500478p
_journal_volume                  14
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C7 H17 N O5'
_chemical_formula_sum            'C7 H17 N O5'
_chemical_formula_weight         195.21
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                104.662(13)
_cell_angle_beta                 93.985(14)
_cell_angle_gamma                92.586(14)
_cell_formula_units_Z            1
_cell_length_a                   4.819(6)
_cell_length_b                   5.131(6)
_cell_length_c                   9.627(11)
_cell_measurement_temperature    100(2)
_cell_volume                     229.2(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.927
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3423
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.083
_diffrn_reflns_theta_min         2.195
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       plate
_exptl_crystal_F_000             106
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1762
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0440P)²+0.0982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                1693
_reflns_number_total             1762
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500478p_si_001.cif
_cod_data_source_block           MEG_II
_cod_depositor_comments
'Adding full bibliography for 4511819--4511822.cif.'
_cod_database_code               4511822
#BEGIN Tags that were not found in dictionaries:
_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   0.979
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O -0.0807(4) 0.2538(4) 0.3809(2) 0.0146(5) Uani 1 1 d . .
H1 H -0.031(9) 0.118(9) 0.335(5) 0.018 Uiso 1 1 d . U
O2 O 0.4208(5) 0.2433(4) 0.2274(2) 0.0153(5) Uani 1 1 d . .
H2 H 0.544(10) 0.261(9) 0.278(5) 0.018 Uiso 1 1 d . U
O3 O -0.0605(4) 0.7487(4) 0.1937(2) 0.0142(5) Uani 1 1 d . .
H3 H -0.212(10) 0.721(8) 0.148(4) 0.017 Uiso 1 1 d . U
O4 O 0.4400(4) 0.7386(4) 0.0479(2) 0.0136(5) Uani 1 1 d . .
H4 H 0.375(9) 0.880(9) 0.085(5) 0.016 Uiso 1 1 d . U
O5 O 0.1908(5) 0.5866(4) -0.2299(2) 0.0151(5) Uani 1 1 d . .
H5 H 0.315(9) 0.514(9) -0.240(5) 0.018 Uiso 1 1 d . U
N1 N -0.3302(5) 0.2818(5) -0.2979(3) 0.0135(5) Uani 1 1 d . .
H1N H -0.235(8) 0.350(8) -0.357(4) 0.016 Uiso 1 1 d . U
C1 C 0.1270(7) 0.4750(6) 0.4071(3) 0.0146(6) Uani 1 1 d . .
H1A H 0.2660 0.4593 0.4847 0.017 Uiso 1 1 calc R U
H1B H 0.0366 0.6466 0.4410 0.017 Uiso 1 1 calc R U
C2 C 0.2766(6) 0.4844(6) 0.2739(3) 0.0116(6) Uani 1 1 d . .
H2A H 0.4156 0.6433 0.2991 0.014 Uiso 1 1 calc R U
C3 C 0.0793(7) 0.5061(6) 0.1463(3) 0.0130(6) Uani 1 1 d . .
H3A H -0.0609 0.3481 0.1206 0.016 Uiso 1 1 calc R U
C4 C 0.2358(6) 0.5149(6) 0.0135(3) 0.0119(6) Uani 1 1 d . .
H4A H 0.3372 0.3458 -0.0132 0.014 Uiso 1 1 calc R U
C5 C 0.0405(6) 0.5247(6) -0.1184(3) 0.0131(6) Uani 1 1 d . .
H5A H -0.0898 0.6705 -0.0868 0.016 Uiso 1 1 calc R U
C6 C -0.1340(6) 0.2584(6) -0.1787(3) 0.0135(6) Uani 1 1 d . .
H6A H -0.0101 0.1111 -0.2136 0.016 Uiso 1 1 calc R U
H6B H -0.2382 0.2137 -0.1018 0.016 Uiso 1 1 calc R U
C7 C -0.4573(7) 0.0163(7) -0.3789(3) 0.0182(7) Uani 1 1 d . .
H7A H -0.5680 -0.0614 -0.3158 0.027 Uiso 1 1 calc R U
H7B H -0.3104 -0.1036 -0.4138 0.027 Uiso 1 1 calc R U
H7C H -0.5783 0.0368 -0.4611 0.027 Uiso 1 1 calc R U
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 113(3)
C2 O2 H2 105(3)
C3 O3 H3 106(3)
C4 O4 H4 113(3)
C5 O5 H5 111(3)
C6 N1 C7 111.3(2)
C6 N1 H1N 108(2)
C7 N1 H1N 108(3)
O1 C1 C2 113.0(2)
O1 C1 H1A 109.0
C2 C1 H1A 109.0
O1 C1 H1B 109.0
C2 C1 H1B 109.0
H1A C1 H1B 107.8
O2 C2 C1 109.9(2)
O2 C2 C3 107.2(2)
C1 C2 C3 113.3(2)
O2 C2 H2A 108.8
C1 C2 H2A 108.8
C3 C2 H2A 108.8
O3 C3 C2 106.5(2)
O3 C3 C4 110.3(2)
C2 C3 C4 112.1(2)
O3 C3 H3A 109.3
C2 C3 H3A 109.3
C4 C3 H3A 109.3
O4 C4 C3 110.4(2)
O4 C4 C5 110.4(3)
C3 C4 C5 113.1(3)
O4 C4 H4A 107.6
C3 C4 H4A 107.6
C5 C4 H4A 107.6
O5 C5 C6 109.3(2)
O5 C5 C4 111.8(3)
C6 C5 C4 111.4(2)
O5 C5 H5A 108.1
C6 C5 H5A 108.1
C4 C5 H5A 108.1
N1 C6 C5 109.8(2)
N1 C6 H6A 109.7
C5 C6 H6A 109.7
N1 C6 H6B 109.7
C5 C6 H6B 109.7
H6A C6 H6B 108.2
N1 C7 H7A 109.5
N1 C7 H7B 109.5
H7A C7 H7B 109.5
N1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.439(4)
O1 H1 0.78(5)
O2 C2 1.433(4)
O2 H2 0.73(5)
O3 C3 1.429(4)
O3 H3 0.81(5)
O4 C4 1.434(4)
O4 H4 0.81(5)
O5 C5 1.428(4)
O5 H5 0.72(4)
N1 C6 1.468(4)
N1 C7 1.470(4)
N1 H1N 0.88(4)
C1 C2 1.524(4)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.530(4)
C2 H2A 1.0000
C3 C4 1.538(4)
C3 H3A 1.0000
C4 C5 1.540(4)
C4 H4A 1.0000
C5 C6 1.529(4)
C5 H5A 1.0000
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
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 O3 0.78(5) 2.03(5) 2.767(4) 158(4) 1_545
O2 H2 O1 0.73(5) 2.01(5) 2.722(4) 167(5) 1_655
O3 H3 O4 0.81(5) 1.89(5) 2.692(4) 168(4) 1_455
O4 H4 O2 0.81(5) 2.00(5) 2.735(4) 149(4) 1_565
O5 H5 N1 0.72(4) 2.15(4) 2.867(4) 173(5) 1_655
N1 H1N O1 0.88(4) 2.62(4) 3.367(5) 144(3) 1_554
C7 H7A O5 0.98 2.45 3.376(4) 157.6 1_445
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 O2 -61.6(3)
O1 C1 C2 C3 58.2(3)
O2 C2 C3 O3 -179.3(3)
C1 C2 C3 O3 59.3(3)
O2 C2 C3 C4 -58.6(3)
C1 C2 C3 C4 -179.9(3)
O3 C3 C4 O4 60.3(3)
C2 C3 C4 O4 -58.2(3)
O3 C3 C4 C5 -63.9(3)
C2 C3 C4 C5 177.6(2)
O4 C4 C5 O5 44.2(3)
C3 C4 C5 O5 168.4(2)
O4 C4 C5 C6 166.8(2)
C3 C4 C5 C6 -69.0(3)
C7 N1 C6 C5 167.5(3)
O5 C5 C6 N1 -59.7(3)
C4 C5 C6 N1 176.2(2)
