#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/58/1515844.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_1515844
loop_
_publ_author_name
'Movassaghi, Mohammad'
'Siegel, Dustin S.'
'Han, Sunkyu'
_publ_section_title
;
 Total synthesis of all (-)-Agelastatin alkaloids.
;
_journal_issue                   5
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              561
_journal_page_last               566
_journal_paper_doi               10.1039/c0sc00351d
_journal_volume                  1
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C11 H13 Br N2 O4'
_chemical_formula_weight         317.14
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4061(9)
_cell_length_b                   9.2037(10)
_cell_length_c                   17.3522(18)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.81
_cell_measurement_theta_min      2.42
_cell_volume                     1342.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35594
_diffrn_reflns_theta_full        29.56
_diffrn_reflns_theta_max         29.56
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    3.070
_exptl_absorpt_correction_T_max  0.6559
_exptl_absorpt_correction_T_min  0.4129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3764
_refine_ls_number_restraints     155
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0287P)²+0.3533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                3605
_reflns_number_total             3764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0sc00351d.txt
_cod_data_source_block           10011
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1515844
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.45303(2) 1.23443(2) 0.761152(11) 0.02535(6) Uani 1 1 d U
O3 O -0.05881(15) 1.10047(13) 0.75964(7) 0.0224(2) Uani 1 1 d U
O1 O 0.37837(13) 0.75117(15) 0.50300(7) 0.0211(3) Uani 1 1 d U
C11 C 0.43144(19) 0.94398(17) 0.58949(9) 0.0129(3) Uani 1 1 d U
C8 C 0.1060(2) 1.00163(17) 0.59190(9) 0.0133(3) Uani 1 1 d U
H8 H -0.0075 0.9846 0.6065 0.016 Uiso 1 1 calc R
C13 C 0.49127(19) 1.10630(17) 0.67985(9) 0.0149(3) Uani 1 1 d U
O2 O 0.11365(15) 1.12359(13) 0.54253(7) 0.0180(3) Uani 1 1 d U
C6 C 0.16386(19) 0.94340(17) 0.73314(10) 0.0148(3) Uani 1 1 d U
H6A H 0.1454 0.8430 0.7148 0.018 Uiso 1 1 calc R
H6B H 0.2569 0.9420 0.7681 0.018 Uiso 1 1 calc R
N9 N 0.16809(17) 0.87074(16) 0.55612(8) 0.0147(3) Uani 1 1 d DU
H9 H 0.107(2) 0.820(2) 0.5292(12) 0.018 Uiso 1 1 d D
C7 C 0.19942(18) 1.04208(17) 0.66415(9) 0.0121(3) Uani 1 1 d U
H7 H 0.1718 1.1442 0.6786 0.014 Uiso 1 1 calc R
C10 C 0.32703(19) 0.84818(18) 0.54510(9) 0.0144(3) Uani 1 1 d U
N12 N 0.36849(16) 1.03679(15) 0.64430(8) 0.0129(3) Uani 1 1 d U
C5 C 0.01938(19) 0.99545(16) 0.77685(9) 0.0146(3) Uani 1 1 d U
O4 O -0.00977(17) 0.91247(14) 0.83815(8) 0.0256(3) Uani 1 1 d U
C14 C 0.6335(2) 1.06253(19) 0.64770(10) 0.0163(3) Uani 1 1 d U
H14 H 0.7367 1.0959 0.6613 0.020 Uiso 1 1 calc R
C16 C -0.1439(3) 0.9579(2) 0.88503(13) 0.0295(5) Uani 1 1 d U
H16A H -0.1233 1.0550 0.9060 0.044 Uiso 1 1 calc R
H16B H -0.1588 0.8890 0.9275 0.044 Uiso 1 1 calc R
H16C H -0.2402 0.9605 0.8532 0.044 Uiso 1 1 calc R
C15 C 0.5961(2) 0.95844(18) 0.59068(10) 0.0152(3) Uani 1 1 d U
H15 H 0.6697 0.9077 0.5590 0.018 Uiso 1 1 calc R
C17 C 0.0016(3) 1.1172(3) 0.48062(13) 0.0346(5) Uani 1 1 d U
H17A H 0.0261 1.0338 0.4475 0.052 Uiso 1 1 calc R
H17B H 0.0079 1.2068 0.4503 0.052 Uiso 1 1 calc R
H17C H -0.1060 1.1065 0.5016 0.052 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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
N12 C11 C15 108.14(14)
N12 C11 C10 120.30(14)
C15 C11 C10 131.49(15)
O2 C8 N9 112.54(14)
O2 C8 C7 106.33(13)
N9 C8 C7 111.66(13)
N12 C13 C14 109.66(14)
N12 C13 Br1 120.57(12)
C14 C13 Br1 129.74(12)
C8 O2 C17 113.14(14)
C5 C6 C7 111.19(13)
C10 N9 C8 122.51(14)
N12 C7 C8 107.35(13)
N12 C7 C6 110.72(13)
C8 C7 C6 113.40(13)
O1 C10 N9 122.42(15)
O1 C10 C11 122.61(15)
N9 C10 C11 114.93(14)
C13 N12 C11 108.15(13)
C13 N12 C7 127.87(14)
C11 N12 C7 123.63(13)
O3 C5 O4 123.83(16)
O3 C5 C6 124.62(15)
O4 C5 C6 111.54(14)
C5 O4 C16 115.14(14)
C13 C14 C15 106.74(15)
C11 C15 C14 107.28(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.8667(16)
O3 C5 1.2064(19)
O1 C10 1.232(2)
C11 N12 1.384(2)
C11 C15 1.390(2)
C11 C10 1.463(2)
C8 O2 1.4135(19)
C8 N9 1.452(2)
C8 C7 1.525(2)
C13 N12 1.362(2)
C13 C14 1.379(2)
O2 C17 1.430(2)
C6 C5 1.510(2)
C6 C7 1.532(2)
N9 C10 1.366(2)
C7 N12 1.463(2)
C5 O4 1.3321(19)
O4 C16 1.452(2)
C14 C15 1.413(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102231012
