#------------------------------------------------------------------------------
#$Date: 2019-12-26 22:28:27 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/19/2311964.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_2311964
loop_
_publ_author_name
'Roque-Flores, Roxana L'
'Guzei, Ilia A.'
'Matos, Jivaldo do Rosario'
'Yu, Lian'
_publ_section_title
;
 Polymorphs of the antiviral drug ganciclovir.
;
_journal_coeditor_code           QP3002
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              1116
_journal_page_last               1120
_journal_paper_doi               10.1107/S2053229617016059
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C9 H13 N5 O4'
_chemical_formula_moiety         'C9 H13 N5 O4'
_chemical_formula_sum            'C9 H13 N5 O4'
_chemical_formula_weight         255.24
_chemical_name_systematic
2-Amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.06.28 svn.r3296 for OlexSys, GUI svn.r5195)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.632(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6448(10)
_cell_length_b                   15.632(3)
_cell_length_c                   14.130(3)
_cell_measurement_reflns_used    5037
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.527
_cell_measurement_theta_min      2.885
_cell_volume                     1025.5(4)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and
Gn (Guzei (2013)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII area detector'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45424
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_min         1.943
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  .99
_exptl_absorpt_correction_T_min  .54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         45424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0535
_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)+0.6622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                38287
_reflns_number_total             45424
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qp3002sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311964
_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   0.927
_shelx_estimated_absorpt_t_max   0.987
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.8794(3) 0.29596(9) 0.67663(10) 0.0163(3) Uani d 1
O O2 0.4005(3) 0.40726(9) 0.25113(9) 0.0144(3) Uani d 1
O O3 0.2212(3) 0.38278(9) -0.00228(9) 0.0156(3) Uani d 1
H H3 0.094(7) 0.340(2) -0.007(2) 0.047(9) Uiso d 1
O O4 0.5480(3) 0.55219(9) 0.16460(10) 0.0158(3) Uani d 1
H H4 0.617(6) 0.575(2) 0.116(2) 0.042(9) Uiso d 1
N N1 0.1570(3) 0.49144(11) 0.62555(12) 0.0147(3) Uani d 1
H H1A 0.032(5) 0.5186(17) 0.591(2) 0.024(7) Uiso d 1
H H1B 0.220(6) 0.5137(19) 0.680(2) 0.029(7) Uiso d 1
N N2 0.5152(3) 0.39079(11) 0.64408(12) 0.0127(3) Uani d 1
H H2 0.510(5) 0.4037(17) 0.699(2) 0.024(7) Uiso d 1
N N3 0.8130(3) 0.24735(10) 0.46481(11) 0.0132(3) Uani d 1
N N4 0.4703(3) 0.31416(10) 0.37787(11) 0.0126(3) Uani d 1
N N5 0.2822(3) 0.41260(10) 0.49414(11) 0.0119(3) Uani d 1
C C1 0.3186(4) 0.43137(12) 0.58517(13) 0.0120(3) Uani d 1
C C2 0.7116(4) 0.32817(12) 0.61743(13) 0.0126(3) Uani d 1
C C3 0.6763(4) 0.30842(12) 0.51948(13) 0.0125(3) Uani d 1
C C4 0.6837(4) 0.25277(12) 0.38132(13) 0.0136(4) Uani d 1
H H4A 0.7319 0.2181 0.3288 0.016 Uiso calc 1
C C5 0.4636(4) 0.34996(12) 0.46676(12) 0.0115(3) Uani d 1
C C6 0.2863(4) 0.33450(12) 0.29719(13) 0.0138(4) Uani d 1
H H6A 0.2773 0.2854 0.2530 0.017 Uiso calc 1
H H6B 0.0888 0.3468 0.3180 0.017 Uiso calc 1
C C7 0.2467(4) 0.42577(12) 0.16349(13) 0.0123(3) Uani d 1
H H7 0.0410 0.4081 0.1691 0.015 Uiso calc 1
C C8 0.3819(4) 0.37434(13) 0.08467(13) 0.0156(4) Uani d 1
H H8A 0.5815 0.3945 0.0758 0.019 Uiso calc 1
H H8B 0.3904 0.3133 0.1030 0.019 Uiso calc 1
C C9 0.2598(4) 0.52153(12) 0.14811(13) 0.0141(4) Uani d 1
H H9A 0.1956 0.5352 0.0824 0.017 Uiso calc 1
H H9B 0.1283 0.5505 0.1918 0.017 Uiso calc 1
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
C6 O2 C7 111.84(13)
C8 O3 H3 109(2)
C9 O4 H4 112(2)
H1A N1 H1B 120(3)
C1 N1 H1A 118.8(19)
C1 N1 H1B 117.9(18)
C1 N2 H2 115.7(19)
C1 N2 C2 126.04(16)
C2 N2 H2 118.3(19)
C4 N3 C3 104.51(15)
C4 N4 C6 126.23(16)
C5 N4 C4 106.57(15)
C5 N4 C6 127.18(16)
C1 N5 C5 111.93(15)
N1 C1 N2 115.89(16)
N5 C1 N1 120.71(17)
N5 C1 N2 123.39(17)
O1 C2 N2 120.52(17)
O1 C2 C3 128.58(18)
N2 C2 C3 110.86(16)
N3 C3 C2 130.29(17)
C5 C3 N3 110.68(16)
C5 C3 C2 118.89(17)
N3 C4 N4 112.77(17)
N3 C4 H4A 123.6
N4 C4 H4A 123.6
N4 C5 C3 105.47(16)
N5 C5 N4 125.76(16)
N5 C5 C3 128.77(17)
O2 C6 N4 108.58(14)
O2 C6 H6A 110.0
O2 C6 H6B 110.0
N4 C6 H6A 110.0
N4 C6 H6B 110.0
H6A C6 H6B 108.4
O2 C7 H7 109.1
O2 C7 C8 108.53(15)
O2 C7 C9 107.51(14)
C8 C7 H7 109.1
C9 C7 H7 109.1
C9 C7 C8 113.43(16)
O3 C8 C7 111.39(15)
O3 C8 H8A 109.4
O3 C8 H8B 109.4
C7 C8 H8A 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
O4 C9 C7 110.37(15)
O4 C9 H9A 109.6
O4 C9 H9B 109.6
C7 C9 H9A 109.6
C7 C9 H9B 109.6
H9A C9 H9B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.234(2)
O2 C6 1.421(2)
O2 C7 1.441(2)
O3 H3 0.89(3)
O3 C8 1.425(2)
O4 H4 0.85(3)
O4 C9 1.435(2)
N1 H1A 0.86(3)
N1 H1B 0.88(3)
N1 C1 1.340(2)
N2 H2 0.80(3)
N2 C1 1.373(2)
N2 C2 1.397(2)
N3 C3 1.393(2)
N3 C4 1.311(2)
N4 C4 1.380(2)
N4 C5 1.376(2)
N4 C6 1.440(2)
N5 C1 1.326(2)
N5 C5 1.355(2)
C2 C3 1.423(3)
C3 C5 1.382(2)
C4 H4A 0.9500
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7 1.0000
C7 C8 1.523(3)
C7 C9 1.514(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 N3 4_465 0.89(3) 1.93(3) 2.811(2) 172(3)
O4 H4 O3 3_665 0.85(3) 1.91(4) 2.754(2) 176(3)
N1 H1A N5 3_566 0.86(3) 2.15(3) 3.012(2) 179(3)
N1 H1B O2 3_666 0.88(3) 2.34(3) 3.093(2) 143(2)
N2 H2 O4 3_666 0.80(3) 2.07(3) 2.869(2) 172(3)
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 C2 C3 N3 1.7(3)
O1 C2 C3 C5 176.87(18)
O2 C7 C8 O3 173.90(14)
O2 C7 C9 O4 46.58(19)
N2 C2 C3 N3 -176.04(18)
N2 C2 C3 C5 -0.9(2)
N3 C3 C5 N4 -0.3(2)
N3 C3 C5 N5 179.48(17)
C1 N2 C2 O1 179.91(17)
C1 N2 C2 C3 -2.1(3)
C1 N5 C5 N4 177.25(17)
C1 N5 C5 C3 -2.5(3)
C2 N2 C1 N1 -178.02(17)
C2 N2 C1 N5 3.2(3)
C2 C3 C5 N4 -176.35(16)
C2 C3 C5 N5 3.4(3)
C3 N3 C4 N4 0.2(2)
C4 N3 C3 C2 175.54(19)
C4 N3 C3 C5 0.1(2)
C4 N4 C5 N5 -179.39(17)
C4 N4 C5 C3 0.39(19)
C4 N4 C6 O2 -98.1(2)
C5 N4 C4 N3 -0.4(2)
C5 N4 C6 O2 83.8(2)
C5 N5 C1 N1 -179.50(17)
C5 N5 C1 N2 -0.8(2)
C6 O2 C7 C8 -87.48(18)
C6 O2 C7 C9 149.46(15)
C6 N4 C4 N3 -178.82(17)
C6 N4 C5 N5 -1.0(3)
C6 N4 C5 C3 178.81(17)
C7 O2 C6 N4 173.40(14)
C8 C7 C9 O4 -73.42(19)
C9 C7 C8 O3 -66.7(2)
