#------------------------------------------------------------------------------
#$Date: 2019-11-03 14:24:39 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221639 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/85/4128559.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_4128559
loop_
_publ_author_name
'Zhang, Weicheng'
'Pal, Ayan'
'Ricardo, Alonso'
'Szostak, Jack W.'
_publ_section_title
;
 Template-Directed Nonenzymatic Primer Extension Using
 2-Methylimidazole-Activated Morpholino Derivatives of Guanosine and
 Cytidine.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12159
_journal_page_last               12166
_journal_paper_doi               10.1021/jacs.9b06453
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H16 N4 O4'
_chemical_formula_weight         244.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3359(4)
_cell_length_b                   11.5375(5)
_cell_length_c                   11.8279(5)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.7
_cell_measurement_theta_min      3.83
_cell_volume                     1137.55(9)
_computing_cell_refinement       'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23324
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.705
_diffrn_reflns_theta_max         66.705
_diffrn_reflns_theta_min         5.356
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.8058
_exptl_absorpt_correction_T_min  0.7474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.0095(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0233
_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)+(0.0356P)²+0.2472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1988
_reflns_number_total             1995
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b06453_si_002.cif
_cod_data_source_block           MorCNucl
_cod_database_code               4128559
_shelx_shelxl_version_number     2014/7
_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   0.846
_shelx_estimated_absorpt_t_max   0.877
loop_
_space_group_symop_operation_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'
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 0.78587(14) 0.94590(10) -0.01198(10) 0.0167(3) Uani 1 1 d . .
H1 H 0.879(3) 0.920(2) -0.041(2) 0.039(7) Uiso 1 1 d . .
O2 O 0.71977(14) 0.79169(10) 0.25257(9) 0.0164(3) Uani 1 1 d . .
O3 O 0.75019(16) 0.49100(10) 0.42234(10) 0.0208(3) Uani 1 1 d . .
N1 N 0.55596(18) 0.63196(12) 0.10857(11) 0.0155(3) Uani 1 1 d . .
H1A H 0.635(3) 0.5828(19) 0.0838(18) 0.022(5) Uiso 1 1 d . .
N2 N 0.67632(16) 0.68071(12) 0.41199(11) 0.0147(3) Uani 1 1 d . .
N3 N 0.69865(17) 0.58333(12) 0.58831(11) 0.0154(3) Uani 1 1 d . .
N4 N 0.64887(18) 0.68324(13) 0.75248(12) 0.0171(3) Uani 1 1 d . .
H4A H 0.677(2) 0.6244(19) 0.7931(16) 0.015(5) Uiso 1 1 d . .
H4B H 0.611(3) 0.749(2) 0.7863(18) 0.021(5) Uiso 1 1 d . .
C1 C 0.7733(2) 0.92515(14) 0.10602(13) 0.0174(4) Uani 1 1 d . .
H1B H 0.6854 0.9730 0.1375 0.021 Uiso 1 1 calc R U
H1C H 0.8744 0.9488 0.1434 0.021 Uiso 1 1 calc R U
C2 C 0.7404(2) 0.79805(13) 0.13147(13) 0.0144(3) Uani 1 1 d . .
H2 H 0.8357 0.7507 0.1090 0.017 Uiso 1 1 calc R U
C3 C 0.5925(2) 0.75110(14) 0.07312(14) 0.0164(4) Uani 1 1 d . .
H3A H 0.4998 0.8016 0.0907 0.020 Uiso 1 1 calc R U
H3B H 0.6093 0.7527 -0.0097 0.020 Uiso 1 1 calc R U
C4 C 0.5460(2) 0.62443(15) 0.23246(13) 0.0157(4) Uani 1 1 d . .
H4C H 0.5351 0.5422 0.2551 0.019 Uiso 1 1 calc R U
H4D H 0.4494 0.6664 0.2589 0.019 Uiso 1 1 calc R U
C5 C 0.6940(2) 0.67595(14) 0.28809(12) 0.0144(3) Uani 1 1 d . .
H5 H 0.7899 0.6279 0.2684 0.017 Uiso 1 1 calc R U
C6 C 0.71019(19) 0.58028(14) 0.47341(13) 0.0147(3) Uani 1 1 d . .
C7 C 0.65311(19) 0.68130(15) 0.64011(13) 0.0147(4) Uani 1 1 d . .
C8 C 0.6105(2) 0.78272(14) 0.57812(14) 0.0180(4) Uani 1 1 d . .
H8 H 0.5731 0.8504 0.6154 0.022 Uiso 1 1 calc R U
C9 C 0.6252(2) 0.77913(14) 0.46499(14) 0.0175(4) Uani 1 1 d . .
H9 H 0.5998 0.8458 0.4214 0.021 Uiso 1 1 calc R U
O1W O 0.45146(16) 0.41460(10) 0.66674(10) 0.0193(3) Uani 1 1 d . .
H1WA H 0.529(4) 0.457(2) 0.648(2) 0.045(8) Uiso 1 1 d . .
H1WB H 0.371(3) 0.432(2) 0.615(2) 0.034(6) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 112.2(16)
C5 O2 C2 111.11(11)
C3 N1 C4 110.58(13)
C3 N1 H1A 109.9(13)
C4 N1 H1A 108.8(14)
C9 N2 C6 120.95(13)
C9 N2 C5 121.25(13)
C6 N2 C5 117.78(13)
C7 N3 C6 119.83(14)
C7 N4 H4A 122.3(13)
C7 N4 H4B 117.5(13)
H4A N4 H4B 120.1(18)
O1 C1 C2 111.73(13)
O1 C1 H1B 109.3
C2 C1 H1B 109.3
O1 C1 H1C 109.3
C2 C1 H1C 109.3
H1B C1 H1C 107.9
O2 C2 C3 109.69(13)
O2 C2 C1 105.46(12)
C3 C2 C1 113.67(14)
O2 C2 H2 109.3
C3 C2 H2 109.3
C1 C2 H2 109.3
N1 C3 C2 111.94(13)
N1 C3 H3A 109.2
C2 C3 H3A 109.2
N1 C3 H3B 109.2
C2 C3 H3B 109.2
H3A C3 H3B 107.9
N1 C4 C5 111.25(13)
N1 C4 H4C 109.4
C5 C4 H4C 109.4
N1 C4 H4D 109.4
C5 C4 H4D 109.4
H4C C4 H4D 108.0
O2 C5 N2 105.96(12)
O2 C5 C4 111.33(13)
N2 C5 C4 111.36(13)
O2 C5 H5 109.4
N2 C5 H5 109.4
C4 C5 H5 109.4
O3 C6 N3 121.75(14)
O3 C6 N2 119.36(14)
N3 C6 N2 118.88(13)
N4 C7 N3 118.58(15)
N4 C7 C8 119.58(15)
N3 C7 C8 121.84(14)
C9 C8 C7 117.63(15)
C9 C8 H8 121.2
C7 C8 H8 121.2
C8 C9 N2 120.74(15)
C8 C9 H9 119.6
N2 C9 H9 119.6
H1WA O1W H1WB 105(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4199(18)
O1 H1 0.90(3)
O2 C5 1.416(2)
O2 C2 1.4445(17)
O3 C6 1.240(2)
N1 C3 1.469(2)
N1 C4 1.470(2)
N1 H1A 0.91(2)
N2 C9 1.365(2)
N2 C6 1.396(2)
N2 C5 1.4738(18)
N3 C7 1.341(2)
N3 C6 1.3629(19)
N4 C7 1.330(2)
N4 H4A 0.86(2)
N4 H4B 0.91(2)
C1 C2 1.522(2)
C1 H1B 0.9900
C1 H1C 0.9900
C2 C3 1.513(2)
C2 H2 1.0000
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.519(2)
C4 H4C 0.9900
C4 H4D 0.9900
C5 H5 1.0000
C7 C8 1.426(2)
C8 C9 1.344(2)
C8 H8 0.9500
C9 H9 0.9500
O1W H1WA 0.84(3)
O1W H1WB 0.93(3)
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 N1 0.90(3) 1.78(3) 2.6798(18) 175(2) 4_565
N1 H1A O3 0.91(2) 2.30(2) 3.0783(19) 142.6(18) 2_664
N4 H4A O3 0.86(2) 2.12(2) 2.9640(19) 166.9(18) 2_665
N4 H4B O1W 0.91(2) 2.06(2) 2.956(2) 167.6(19) 3_656
O1W H1WB O1 0.93(3) 1.80(3) 2.7195(17) 172(2) 3_645
O1W H1WA N3 0.84(3) 2.15(3) 2.9826(19) 171(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
C5 O2 C2 C3 59.38(16)
C5 O2 C2 C1 -177.83(13)
O1 C1 C2 O2 -176.15(13)
O1 C1 C2 C3 -55.95(18)
C4 N1 C3 C2 53.34(18)
O2 C2 C3 N1 -56.57(16)
C1 C2 C3 N1 -174.34(13)
C3 N1 C4 C5 -51.92(18)
C2 O2 C5 N2 179.49(12)
C2 O2 C5 C4 -59.29(16)
C9 N2 C5 O2 25.3(2)
C6 N2 C5 O2 -156.12(13)
C9 N2 C5 C4 -95.92(18)
C6 N2 C5 C4 82.68(17)
N1 C4 C5 O2 55.49(17)
N1 C4 C5 N2 173.50(13)
C7 N3 C6 O3 -179.20(15)
C7 N3 C6 N2 1.0(2)
C9 N2 C6 O3 177.14(15)
C5 N2 C6 O3 -1.5(2)
C9 N2 C6 N3 -3.0(2)
C5 N2 C6 N3 178.37(14)
C6 N3 C7 N4 -177.42(15)
C6 N3 C7 C8 2.2(2)
N4 C7 C8 C9 176.27(16)
N3 C7 C8 C9 -3.3(3)
C7 C8 C9 N2 1.2(3)
C6 N2 C9 C8 1.9(3)
C5 N2 C9 C8 -179.60(16)
