#------------------------------------------------------------------------------
#$Date: 2019-06-20 16:16:19 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/18/1551806.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_1551806
loop_
_publ_author_name
'KAWAMURA, Tomoko'
'HIRAYAMA, Noriaki'
_publ_section_title
;
 Crystal Structure of Ganciclovir
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              51
_journal_paper_doi               10.2116/xraystruct.25.51
_journal_volume                  25
_journal_year                    2009
_chemical_formula_moiety         'C9 H13 N5 O4 '
_chemical_formula_sum            'C9 H13 N5 O4'
_chemical_formula_weight         255.23
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.11(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   4.3803(15)
_cell_length_b                   10.909(4)
_cell_length_c                   11.601(4)
_cell_measurement_reflns_used    3118
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      3.9
_cell_volume                     547.4(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.087
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4252
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.09
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             268.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.78
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1712
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.005
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(Fo)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                489
_reflns_number_total             1713
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            25_51_1.cif
_cod_data_source_block           '_ganciclovir'
_cod_original_cell_volume        547.3(3)
_cod_original_formula_sum        'C9 H13 N5 O4 '
_cod_database_code               1551806
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O(1) O -0.1265(15) 0.6191(7) -0.0669(5) 0.073(2) Uani 1.00 1 d .
O(2) O 0.7514(16) 0.7149(5) 0.4244(5) 0.064(2) Uani 1.00 1 d .
O(3) O 0.835(2) 0.4568(10) 0.4523(8) 0.129(4) Uani 1.00 1 d .
O(4) O 1.1130(16) 0.6311(8) 0.7169(5) 0.099(3) Uani 1.00 1 d .
N(1) N 0.176(2) 0.4855(8) 0.0498(7) 0.061(3) Uani 1.00 1 d .
N(2) N 0.579(2) 0.5349(7) 0.2074(7) 0.055(3) Uani 1.00 1 d .
N(3) N 0.225(2) 0.8184(8) 0.0878(7) 0.060(3) Uani 1.00 1 d .
N(4) N 0.610(2) 0.7571(8) 0.2300(7) 0.057(3) Uani 1.00 1 d .
N(5) N 0.4593(19) 0.3312(7) 0.1581(7) 0.067(3) Uani 1.00 1 d .
C(1) C 0.405(2) 0.4520(9) 0.1387(8) 0.053(4) Uani 1.00 1 d .
C(2) C 0.488(2) 0.6507(11) 0.1780(8) 0.050(3) Uani 1.00 1 d .
C(3) C 0.260(2) 0.6931(10) 0.0907(9) 0.056(4) Uani 1.00 1 d .
C(4) C 0.081(2) 0.6029(11) 0.0186(8) 0.066(4) Uani 1.00 1 d .
C(5) C 0.444(3) 0.8506(10) 0.1726(11) 0.071(4) Uani 1.00 1 d .
C(6) C 0.873(2) 0.7619(8) 0.3266(8) 0.056(3) Uani 1.00 1 d .
C(7) C 0.997(2) 0.6598(12) 0.5070(9) 0.072(4) Uani 1.00 1 d .
C(8) C 1.080(3) 0.5306(11) 0.4592(17) 0.169(8) Uani 1.00 1 d .
C(9) C 0.868(2) 0.6685(11) 0.6245(9) 0.081(4) Uani 1.00 1 d .
H(1) H 0.0638 0.4189 0.0081 0.011 Uiso 1.00 1 c R
H(2) H 0.9374 0.8450 0.3393 0.011 Uiso 1.00 1 c R
H(3) H 1.0461 0.7152 0.3106 0.011 Uiso 1.00 1 c R
H(4) H 0.4892 0.9346 0.1976 0.011 Uiso 1.00 1 c R
H(5) H 1.1780 0.7056 0.5115 0.011 Uiso 1.00 1 c R
H(6) H 0.7030 0.6128 0.6201 0.011 Uiso 1.00 1 c R
H(7) H 0.8209 0.7467 0.6369 0.011 Uiso 1.00 1 c R
H(8) H 0.7192 0.4710 0.4206 0.011 Uiso 1.00 1 c R
H(9) H 0.3399 0.2699 0.1124 0.011 Uiso 1.00 1 c R
H(10) H 0.6225 0.3040 0.2187 0.011 Uiso 1.00 1 c R
H(13) H 1.0141 0.6055 0.7666 0.011 Uiso 1.00 1 c R
H(11) H 1.2202 0.4926 0.5228 0.011 Uiso 1.00 1 c R
H(12) H 1.1553 0.5343 0.3933 0.011 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 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_publ_flag
C(6) O(2) C(7) 110.1(7) yes
C(1) N(1) C(4) 126.9(9) yes
C(1) N(2) C(2) 111.0(8) yes
C(3) N(3) C(5) 100.5(8) yes
C(2) N(4) C(5) 106.1(8) yes
C(2) N(4) C(6) 124.4(8) yes
C(5) N(4) C(6) 129.5(8) yes
N(1) C(1) N(2) 122.7(9) yes
N(1) C(1) N(5) 118.3(9) yes
N(2) C(1) N(5) 119.0(9) yes
N(2) C(2) N(4) 126.7(8) yes
N(2) C(2) C(3) 130.3(10) yes
N(4) C(2) C(3) 102.9(9) yes
N(3) C(3) C(2) 114.5(9) yes
N(3) C(3) C(4) 128.1(9) yes
C(2) C(3) C(4) 117.3(10) yes
O(1) C(4) N(1) 119.5(10) yes
O(1) C(4) C(3) 128.7(11) yes
N(1) C(4) C(3) 111.7(8) yes
N(3) C(5) N(4) 115.9(9) yes
O(2) C(6) N(4) 104.3(7) yes
O(2) C(7) C(8) 109.0(9) yes
O(2) C(7) C(9) 102.5(8) yes
C(8) C(7) C(9) 119.8(11) yes
O(3) C(8) C(7) 109.4(11) yes
O(4) C(9) C(7) 107.4(9) yes
C(8) O(3) H(8) 122.5 no
C(9) O(4) H(13) 101.7 no
C(1) N(1) H(1) 115.5 no
C(4) N(1) H(1) 117.5 no
C(1) N(5) H(9) 121.6 no
C(1) N(5) H(10) 120.7 no
H(9) N(5) H(10) 117.7 no
N(3) C(5) H(4) 124.5 no
N(4) C(5) H(4) 119.6 no
O(2) C(6) H(2) 111.0 no
O(2) C(6) H(3) 111.7 no
N(4) C(6) H(2) 109.1 no
N(4) C(6) H(3) 112.4 no
H(2) C(6) H(3) 108.2 no
O(2) C(7) H(5) 110.5 no
C(8) C(7) H(5) 105.0 no
C(9) C(7) H(5) 110.0 no
O(3) C(8) H(11) 101.0 no
O(3) C(8) H(12) 112.5 no
C(7) C(8) H(11) 105.5 no
C(7) C(8) H(12) 113.8 no
H(11) C(8) H(12) 113.7 no
O(4) C(9) H(6) 109.4 no
O(4) C(9) H(7) 108.2 no
C(7) C(9) H(6) 107.2 no
C(7) C(9) H(7) 108.8 no
H(6) C(9) H(7) 115.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(4) 1.248(11) yes
O(2) C(6) 1.423(12) yes
O(2) C(7) 1.454(12) yes
O(3) C(8) 1.334(17) yes
O(4) C(9) 1.451(12) yes
N(1) C(1) 1.371(13) yes
N(1) C(4) 1.376(15) yes
N(2) C(1) 1.357(13) yes
N(2) C(2) 1.352(14) yes
N(3) C(3) 1.375(14) yes
N(3) C(5) 1.311(15) yes
N(4) C(2) 1.377(14) yes
N(4) C(5) 1.363(14) yes
N(4) C(6) 1.475(12) yes
N(5) C(1) 1.351(13) yes
C(2) C(3) 1.386(14) yes
C(3) C(4) 1.439(15) yes
C(7) C(8) 1.577(19) yes
C(7) C(9) 1.560(16) yes
O(3) H(8) 0.598 no
N(1) H(1) 0.963 no
N(5) H(9) 0.956 no
N(5) H(10) 0.966 no
C(5) H(4) 0.971 no
C(6) H(2) 0.954 no
C(6) H(3) 0.956 no
C(7) H(5) 0.931 no
C(8) H(11) 0.973 no
C(8) H(12) 0.879 no
C(9) H(6) 0.939 no
C(9) H(7) 0.894 no
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_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O(4) H(13) O(1) 1_656 2.870(9) 0.822 2.123 151.0 no
N(1) H(1) N(3) 2_545 2.839(12) 0.963 1.895 166.1 no
N(5) H(9) O(1) 2_545 2.847(11) 0.956 1.924 161.7 no
N(5) H(10) O(4) 2_746 3.084(11) 0.966 2.276 140.6 no
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
C(6) O(2) C(7) C(8) -76.6(11)
C(6) O(2) C(7) C(9) 155.4(8)
C(7) O(2) C(6) N(4) 152.7(7)
C(1) N(1) C(4) O(1) 178.0(11)
C(1) N(1) C(4) C(3) 1.2(17)
C(4) N(1) C(1) N(2) -1.9(19)
C(4) N(1) C(1) N(5) 178.2(11)
C(1) N(2) C(2) N(4) 179.3(10)
C(1) N(2) C(2) C(3) -1.7(16)
C(2) N(2) C(1) N(1) 1.9(15)
C(2) N(2) C(1) N(5) -178.2(10)
C(3) N(3) C(5) N(4) -1.3(14)
C(5) N(3) C(3) C(2) 2.2(13)
C(5) N(3) C(3) C(4) 179.1(12)
C(2) N(4) C(5) N(3) -0.0(14)
C(5) N(4) C(2) N(2) -179.4(11)
C(5) N(4) C(2) C(3) 1.3(12)
C(2) N(4) C(6) O(2) -70.7(11)
C(6) N(4) C(2) N(2) 1.7(17)
C(6) N(4) C(2) C(3) -177.5(9)
C(5) N(4) C(6) O(2) 110.7(12)
C(6) N(4) C(5) N(3) 178.8(10)
N(2) C(2) C(3) N(3) 178.5(10)
N(2) C(2) C(3) C(4) 1.2(18)
N(4) C(2) C(3) N(3) -2.3(13)
N(4) C(2) C(3) C(4) -179.6(9)
N(3) C(3) C(4) O(1) 6(2)
N(3) C(3) C(4) N(1) -177.6(11)
C(2) C(3) C(4) O(1) -177.3(11)
C(2) C(3) C(4) N(1) -0.7(15)
O(2) C(7) C(8) O(3) -63.1(15)
O(2) C(7) C(9) O(4) -172.4(8)
C(8) C(7) C(9) O(4) 66.9(12)
C(9) C(7) C(8) O(3) 54.3(16)
