# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_as368184
_database_code_depnum_ccdc_archive 'CCDC 1969219'
loop_
_audit_author_name
_audit_author_address
'Ashoke Sharon'
;Department of Chemistry, Birla Institute of Technology
India
;
_audit_update_record             
;
2019-12-01 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;
_audit_creation_date             2019-12-01
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
asharon@bitmesra.ac.in
_chemical_name_common            'carbocyclic nucleoside'
_chemical_name_systematic        
(1S,2R,3R,5R)-5-(4-amino-5-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3-(hydroxymethyl)-3-methyl-4-methylenecyclopentane-1,2-diol
_chemical_formula_moiety         'C14 H17 Cl N4 O3'
_chemical_formula_sum            'C14 H17 Cl N4 O3'
_chemical_formula_weight         324.76
_chemical_absolute_configuration ?
_chemical_melting_point          499
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6168(4)
_cell_length_b                   6.7974(3)
_cell_length_c                   13.2395(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.344(4)
_cell_angle_gamma                90
_cell_volume                     765.18(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3022
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.6430
_cell_measurement_theta_min      4.2720
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_preparation       Synthesis
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.379
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4324
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2861
_reflns_number_total             3143
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.043
_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)+(0.0388P)²+0.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.c X=CH2 refined with riding coordinates:
 N22(H22A,H22B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17), O18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl21 Cl 0.32516(12) 0.68348(15) 0.51681(7) 0.0842(3) Uani 1 1 d . . . . .
O17 O 0.6851(2) 0.6239(3) -0.00339(13) 0.0496(5) Uani 1 1 d . . . . .
H17 H 0.660230 0.672572 -0.060387 0.074 Uiso 1 1 calc GR . . . .
O18 O 0.3874(2) 0.7256(3) 0.04165(17) 0.0593(6) Uani 1 1 d . . . . .
H18 H 0.351299 0.834696 0.025074 0.089 Uiso 1 1 calc GR . . . .
O16 O 0.9172(3) 0.8760(4) 0.33110(15) 0.0630(6) Uani 1 1 d . . . . .
N3 N 0.3445(2) 0.2226(3) 0.20882(15) 0.0413(5) Uani 1 1 d . . . . .
N1 N 0.4595(3) 0.5357(3) 0.26025(15) 0.0412(5) Uani 1 1 d . . . . .
N5 N 0.1861(3) 0.0894(4) 0.32519(17) 0.0512(6) Uani 1 1 d . . . . .
N22 N 0.1454(3) 0.2388(4) 0.47347(17) 0.0598(7) Uani 1 1 d . . . . .
H22A H 0.088592 0.139827 0.484960 0.072 Uiso 1 1 calc R . . . .
H22B H 0.159253 0.334901 0.516260 0.072 Uiso 1 1 calc R . . . .
C2 C 0.3690(3) 0.3775(4) 0.27253(17) 0.0352(5) Uani 1 1 d . . . . .
C7 C 0.3062(3) 0.3994(4) 0.36306(18) 0.0373(5) Uani 1 1 d . . . . .
C11 C 0.7314(3) 0.5619(4) 0.21836(17) 0.0364(5) Uani 1 1 d . . . . .
C10 C 0.5552(3) 0.5595(3) 0.17922(17) 0.0350(5) Uani 1 1 d . . . . .
H10 H 0.533243 0.447434 0.132518 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8052(3) 0.7275(4) 0.16559(17) 0.0399(5) Uani 1 1 d . . . . .
C13 C 0.6778(3) 0.7703(4) 0.07264(18) 0.0405(6) Uani 1 1 d . . . . .
H13 H 0.688212 0.903146 0.045731 0.049 Uiso 1 1 calc R . . . .
C6 C 0.2122(3) 0.2435(4) 0.38884(18) 0.0423(6) Uani 1 1 d . . . . .
C14 C 0.5240(3) 0.7463(4) 0.11593(19) 0.0396(5) Uani 1 1 d . . . . .
H14 H 0.510985 0.857402 0.160969 0.048 Uiso 1 1 calc R . . . .
C9 C 0.4578(3) 0.6593(4) 0.3427(2) 0.0511(7) Uani 1 1 d . . . . .
H9 H 0.511955 0.777756 0.353644 0.061 Uiso 1 1 calc R . . . .
C8 C 0.3648(3) 0.5804(4) 0.40503(19) 0.0477(6) Uani 1 1 d . . . . .
C15 C 0.8237(4) 0.9111(5) 0.2349(2) 0.0527(7) Uani 1 1 d . . . . .
C19 C 0.9638(3) 0.6725(6) 0.1357(2) 0.0614(8) Uani 1 1 d . . . . .
H19A H 1.040315 0.655542 0.196376 0.092 Uiso 1 1 calc GR . . . .
H19B H 0.997411 0.775373 0.094496 0.092 Uiso 1 1 calc GR . . . .
H19C H 0.953256 0.551938 0.097370 0.092 Uiso 1 1 calc GR . . . .
C4 C 0.2523(3) 0.0894(4) 0.2405(2) 0.0486(7) Uani 1 1 d . . . . .
C20 C 0.8041(4) 0.4365(5) 0.2845(2) 0.0601(8) Uani 1 1 d . . . . .
H20A H 0.915(4) 0.442(5) 0.305(2) 0.058(9) Uiso 1 1 d . . . . .
H20B H 0.746(4) 0.339(6) 0.315(3) 0.080(12) Uiso 1 1 d . . . . .
H15A H 0.869(3) 1.012(5) 0.199(2) 0.053(8) Uiso 1 1 d . . . . .
H16 H 1.011(5) 0.920(6) 0.337(3) 0.076(11) Uiso 1 1 d . . . . .
H15B H 0.720(4) 0.963(5) 0.250(2) 0.060(9) Uiso 1 1 d . . . . .
H4 H 0.230(3) -0.023(4) 0.199(2) 0.039(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl21 C8 1.721(2) . ?
O17 H17 0.8200 . ?
O17 C13 1.424(3) . ?
O18 H18 0.8200 . ?
O18 C14 1.413(3) . ?
O16 C15 1.412(4) . ?
O16 H16 0.86(4) . ?
N3 C2 1.344(3) . ?
N3 C4 1.318(3) . ?
N1 C2 1.353(3) . ?
N1 C10 1.464(3) . ?
N1 C9 1.380(3) . ?
N5 C6 1.340(3) . ?
N5 C4 1.337(3) . ?
N22 H22A 0.8600 . ?
N22 H22B 0.8600 . ?
N22 C6 1.341(3) . ?
C2 C7 1.401(3) . ?
C7 C6 1.409(4) . ?
C7 C8 1.410(4) . ?
C11 C10 1.523(3) . ?
C11 C12 1.518(3) . ?
C11 C20 1.306(4) . ?
C10 H10 0.9800 . ?
C10 C14 1.521(3) . ?
C12 C13 1.538(3) . ?
C12 C15 1.542(4) . ?
C12 C19 1.530(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.536(4) . ?
C14 H14 0.9800 . ?
C9 H9 0.9300 . ?
C9 C8 1.351(4) . ?
C15 H15A 0.96(3) . ?
C15 H15B 1.01(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C4 H4 0.95(3) . ?
C20 H20A 0.95(3) . ?
C20 H20B 0.96(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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O17 H17 109.5 . . ?
C14 O18 H18 109.5 . . ?
C15 O16 H16 114(3) . . ?
C4 N3 C2 112.3(2) . . ?
C2 N1 C10 125.4(2) . . ?
C2 N1 C9 108.0(2) . . ?
C9 N1 C10 126.3(2) . . ?
C4 N5 C6 118.4(2) . . ?
H22A N22 H22B 120.0 . . ?
C6 N22 H22A 120.0 . . ?
C6 N22 H22B 120.0 . . ?
N3 C2 N1 125.6(2) . . ?
N3 C2 C7 125.2(2) . . ?
N1 C2 C7 109.2(2) . . ?
C2 C7 C6 116.4(2) . . ?
C2 C7 C8 105.5(2) . . ?
C6 C7 C8 138.1(2) . . ?
C12 C11 C10 108.7(2) . . ?
C20 C11 C10 124.4(3) . . ?
C20 C11 C12 126.9(3) . . ?
N1 C10 C11 113.64(19) . . ?
N1 C10 H10 107.6 . . ?
N1 C10 C14 115.2(2) . . ?
C11 C10 H10 107.6 . . ?
C14 C10 C11 104.84(19) . . ?
C14 C10 H10 107.6 . . ?
C11 C12 C13 102.15(19) . . ?
C11 C12 C15 109.7(2) . . ?
C11 C12 C19 113.4(2) . . ?
C13 C12 C15 108.3(2) . . ?
C19 C12 C13 113.0(2) . . ?
C19 C12 C15 110.0(2) . . ?
O17 C13 C12 109.0(2) . . ?
O17 C13 H13 111.7 . . ?
O17 C13 C14 109.2(2) . . ?
C12 C13 H13 111.7 . . ?
C14 C13 C12 103.21(18) . . ?
C14 C13 H13 111.7 . . ?
N5 C6 N22 117.1(2) . . ?
N5 C6 C7 118.7(2) . . ?
N22 C6 C7 124.2(2) . . ?
O18 C14 C10 110.7(2) . . ?
O18 C14 C13 115.0(2) . . ?
O18 C14 H14 109.6 . . ?
C10 C14 C13 102.03(19) . . ?
C10 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
N1 C9 H9 125.5 . . ?
C8 C9 N1 109.0(2) . . ?
C8 C9 H9 125.5 . . ?
C7 C8 Cl21 125.9(2) . . ?
C9 C8 Cl21 125.7(2) . . ?
C9 C8 C7 108.4(2) . . ?
O16 C15 C12 112.9(3) . . ?
O16 C15 H15A 110.5(19) . . ?
O16 C15 H15B 105.8(19) . . ?
C12 C15 H15A 107.1(19) . . ?
C12 C15 H15B 112.9(19) . . ?
H15A C15 H15B 108(3) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C4 N5 129.0(3) . . ?
N3 C4 H4 116.3(16) . . ?
N5 C4 H4 114.7(16) . . ?
C11 C20 H20A 121(2) . . ?
C11 C20 H20B 120(2) . . ?
H20A C20 H20B 119(3) . . ?

_olex2_submission_original_sample_id as368184
_olex2_submission_special_instructions 'No special instructions were received'
