#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180282 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/68/7116812.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_7116812
loop_
_publ_author_name
'E.-K. Kim'
'R. Krishnamurthy'
_publ_section_title
;
 Synthesis of orotidine by intramolecular nucleosidation
;
_journal_name_full               Chem.Commun.
_journal_page_first              5618
_journal_paper_doi               10.1039/C5cc00111K
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H14 N2 O7'
_chemical_formula_sum            'C13 H14 N2 O7'
_chemical_formula_weight         310.26
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.27 svn.r3059 for OlexSys, GUI svn.r4931)
;
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0946(2)
_cell_length_b                   14.4569(5)
_cell_length_c                   18.2887(7)
_cell_measurement_reflns_used    5780
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.829
_cell_measurement_theta_min      3.897
_cell_volume                     1347.00(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16375
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.257
_diffrn_reflns_theta_min         3.897
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.6959.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       Needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0261
_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)+(0.0394P)²+0.1798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2297
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc00111k2.cif
_cod_data_source_block           Krish14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_database_code               7116812
#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_max   0.947
_shelx_estimated_absorpt_t_min   0.831
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4')
3.b Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
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
O1' O 0.2632(3) 0.65048(9) 0.67193(7) 0.0210(3) Uani 1 1 d .
O2 O 0.8408(3) 0.70484(10) 0.52671(7) 0.0231(3) Uani 1 1 d .
O2' O 0.5131(3) 0.52582(10) 0.53508(8) 0.0267(3) Uani 1 1 d .
O3' O 0.2045(3) 0.45792(11) 0.60660(8) 0.0287(3) Uani 1 1 d .
O4 O 1.1915(4) 0.92827(11) 0.67135(10) 0.0377(4) Uani 1 1 d .
O5' O 0.6050(3) 0.62341(10) 0.77431(8) 0.0232(3) Uani 1 1 d .
O7 O 0.4199(3) 0.75776(10) 0.81315(8) 0.0312(4) Uani 1 1 d .
N1 N 0.6776(3) 0.71962(11) 0.64186(9) 0.0210(4) Uani 1 1 d .
N3 N 1.0040(4) 0.81943(12) 0.59902(9) 0.0229(4) Uani 1 1 d D
H3 H 1.106(5) 0.837(2) 0.5636(14) 0.045(8) Uiso 1 1 d D
C1' C 0.4660(4) 0.65331(14) 0.61945(11) 0.0200(4) Uani 1 1 d .
H1' H 0.3893 0.6756 0.5723 0.024 Uiso 1 1 calc R
C2 C 0.8424(4) 0.74527(14) 0.58528(11) 0.0208(4) Uani 1 1 d .
C2' C 0.5671(4) 0.55429(13) 0.60760(11) 0.0205(4) Uani 1 1 d .
H2' H 0.7573 0.5479 0.6202 0.025 Uiso 1 1 calc R
C3' C 0.3923(4) 0.49457(14) 0.65645(11) 0.0228(4) Uani 1 1 d .
H3' H 0.4923 0.4453 0.6829 0.027 Uiso 1 1 calc R
C4 C 1.0380(4) 0.86429(14) 0.66523(12) 0.0263(5) Uani 1 1 d .
C4' C 0.2514(4) 0.56032(13) 0.70786(11) 0.0218(4) Uani 1 1 d .
H4' H 0.0638 0.5409 0.7125 0.026 Uiso 1 1 calc R
C5 C 0.8772(4) 0.82717(14) 0.72376(12) 0.0243(4) Uani 1 1 d .
H5 H 0.8921 0.8518 0.7717 0.029 Uiso 1 1 calc R
C5' C 0.3699(4) 0.56953(14) 0.78355(11) 0.0237(4) Uani 1 1 d .
H5'A H 0.2464 0.6012 0.8170 0.028 Uiso 1 1 calc R
H5'B H 0.4120 0.5079 0.8040 0.028 Uiso 1 1 calc R
C6 C 0.7082(4) 0.75835(13) 0.71046(11) 0.0216(4) Uani 1 1 d .
C7 C 0.5560(4) 0.71560(14) 0.77141(11) 0.0236(4) Uani 1 1 d .
C8 C 0.3265(4) 0.45251(16) 0.53591(12) 0.0282(5) Uani 1 1 d .
C9 C 0.1254(5) 0.4734(3) 0.47810(14) 0.0538(8) Uani 1 1 d .
H9A H 0.0023 0.4215 0.4742 0.081 Uiso 1 1 calc GR
H9B H 0.2135 0.4826 0.4310 0.081 Uiso 1 1 calc GR
H9C H 0.0293 0.5297 0.4913 0.081 Uiso 1 1 calc GR
C10 C 0.4649(7) 0.36112(17) 0.52635(15) 0.0463(7) Uani 1 1 d .
H10A H 0.6012 0.3547 0.5638 0.069 Uiso 1 1 calc GR
H10B H 0.5457 0.3587 0.4778 0.069 Uiso 1 1 calc GR
H10C H 0.3379 0.3106 0.5312 0.069 Uiso 1 1 calc GR
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' C4' 111.24(14)
C2' O2' C8 109.64(15)
C3' O3' C8 107.82(15)
C7 O5' C5' 112.53(15)
C2 N1 C1' 113.78(16)
C6 N1 C1' 126.00(16)
C6 N1 C2 120.13(16)
C2 N3 H3 117(2)
C2 N3 C4 126.88(18)
C4 N3 H3 116(2)
O1' C1' N1 111.04(15)
O1' C1' H1' 108.1
O1' C1' C2' 108.33(15)
N1 C1' H1' 108.1
N1 C1' C2' 113.13(16)
C2' C1' H1' 108.1
O2 C2 N1 121.61(18)
O2 C2 N3 122.56(18)
N3 C2 N1 115.83(17)
O2' C2' C1' 109.73(15)
O2' C2' H2' 112.2
O2' C2' C3' 105.67(15)
C1' C2' H2' 112.2
C3' C2' C1' 104.37(16)
C3' C2' H2' 112.2
O3' C3' C2' 103.15(16)
O3' C3' H3' 112.8
O3' C3' C4' 108.20(17)
C2' C3' H3' 112.8
C4' C3' C2' 106.49(16)
C4' C3' H3' 112.8
O4 C4 N3 121.1(2)
O4 C4 C5 125.2(2)
N3 C4 C5 113.67(18)
O1' C4' C3' 105.11(16)
O1' C4' H4' 109.2
O1' C4' C5' 108.41(16)
C3' C4' H4' 109.2
C5' C4' C3' 115.62(17)
C5' C4' H4' 109.2
C4 C5 H5 119.9
C6 C5 C4 120.29(19)
C6 C5 H5 119.9
O5' C5' C4' 105.78(16)
O5' C5' H5'A 110.6
O5' C5' H5'B 110.6
C4' C5' H5'A 110.6
C4' C5' H5'B 110.6
H5'A C5' H5'B 108.7
N1 C6 C7 116.85(17)
C5 C6 N1 122.57(19)
C5 C6 C7 120.45(18)
O5' C7 C6 109.90(16)
O7 C7 O5' 125.54(19)
O7 C7 C6 124.49(19)
O2' C8 O3' 104.95(16)
O2' C8 C9 107.3(2)
O2' C8 C10 109.79(19)
O3' C8 C9 109.11(19)
O3' C8 C10 110.76(19)
C9 C8 C10 114.4(2)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1' C1' 1.410(2)
O1' C4' 1.461(2)
O2 C2 1.220(2)
O2' C2' 1.416(2)
O2' C8 1.424(3)
O3' C3' 1.424(3)
O3' C8 1.437(3)
O4 C4 1.217(3)
O5' C5' 1.439(3)
O5' C7 1.357(2)
O7 C7 1.198(3)
N1 C1' 1.500(3)
N1 C2 1.383(3)
N1 C6 1.383(3)
N3 H3 0.87(2)
N3 C2 1.375(3)
N3 C4 1.385(3)
C1' H1' 1.0000
C1' C2' 1.537(3)
C2' H2' 1.0000
C2' C3' 1.529(3)
C3' H3' 1.0000
C3' C4' 1.517(3)
C4 C5 1.451(3)
C4' H4' 1.0000
C4' C5' 1.516(3)
C5 H5 0.9500
C5 C6 1.338(3)
C5' H5'A 0.9900
C5' H5'B 0.9900
C6 C7 1.492(3)
C8 C9 1.503(4)
C8 C10 1.508(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 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
N3 H3 O2 0.87(2) 2.13(2) 2.890(2) 146(3) 4_566
