#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/06/1520683.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_1520683
loop_
_publ_author_name
'Johnson, Rebecca E.'
'de Rond, Tristan'
'Lindsay, Vincent N. G.'
'Keasling, Jay D.'
'Sarpong, Richmond'
_publ_section_title
;
 Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a
 Scalemic Mixture.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3474
_journal_page_last               3477
_journal_paper_doi               10.1021/acs.orglett.5b01527
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H24 Cl N3 O'
_chemical_formula_weight         357.87
_chemical_name_common            REJIII-035E2
_chemical_name_systematic        sarpong111
_space_group.centring_type       P
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.793(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8680(8)
_cell_length_b                   6.8325(6)
_cell_length_c                   12.6102(10)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.46
_cell_measurement_theta_min      3.61
_cell_volume                     909.38(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27626
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         69.145
_diffrn_reflns_theta_min         3.609
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.952
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.054(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0467
_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)+(0.0568P)²+0.4776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2912
_reflns_number_total             3342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b01527_si_002.cif
_cod_data_source_block           sarpong111
_cod_depositor_comments
;Adding full bibliography for 1520683.cif.

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               1520683
#BEGIN Tags that were not found in dictionaries:
_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   0.909
_shelx_estimated_absorpt_t_max   0.962
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.5116(3) 0.4446(8) 0.0321(3) 0.0267(7) Uani 1 1 d . .
C2 C 0.6354(3) 0.4400(8) 0.0174(3) 0.0267(8) Uani 1 1 d . .
C3 C 0.6765(4) 0.4333(9) -0.0886(3) 0.0330(9) Uani 1 1 d . .
H3A H 0.6325 0.5373 -0.1381 0.040 Uiso 1 1 calc R U
H3B H 0.6531 0.3054 -0.1247 0.040 Uiso 1 1 calc R U
C4 C 0.8198(4) 0.4627(11) -0.0671(3) 0.0412(10) Uani 1 1 d . .
H4A H 0.8493 0.4161 -0.1311 0.049 Uiso 1 1 calc R U
H4B H 0.8392 0.6041 -0.0581 0.049 Uiso 1 1 calc R U
C5 C 0.8919(4) 0.3536(7) 0.0346(4) 0.0384(11) Uani 1 1 d . .
H5A H 0.9841 0.3683 0.0415 0.046 Uiso 1 1 calc R U
H5B H 0.8712 0.2125 0.0265 0.046 Uiso 1 1 calc R U
C6 C 0.8585(3) 0.4312(8) 0.1392(3) 0.0310(9) Uani 1 1 d . .
H6 H 0.8906 0.3348 0.1990 0.037 Uiso 1 1 calc R U
C7 C 0.7169(3) 0.4397(7) 0.1201(3) 0.0271(8) Uani 1 1 d . .
C8 C 0.6432(3) 0.4486(8) 0.1990(3) 0.0253(7) Uani 1 1 d . .
C9 C 0.3889(3) 0.4436(9) -0.0520(3) 0.0310(8) Uani 1 1 d . .
H9A H 0.3185 0.4458 -0.0157 0.047 Uiso 1 1 calc R U
H9B H 0.3834 0.3251 -0.0966 0.047 Uiso 1 1 calc R U
H9C H 0.3842 0.5593 -0.0987 0.047 Uiso 1 1 calc R U
C10 C 0.9212(4) 0.6271(8) 0.1746(4) 0.0424(12) Uani 1 1 d . .
H10A H 0.8897 0.7251 0.1179 0.064 Uiso 1 1 calc R U
H10B H 1.0132 0.6142 0.1858 0.064 Uiso 1 1 calc R U
H10C H 0.9011 0.6684 0.2430 0.064 Uiso 1 1 calc R U
C11 C 0.6898(3) 0.4557(8) 0.3115(3) 0.0274(7) Uani 1 1 d . .
H11 H 0.7797 0.4512 0.3324 0.033 Uiso 1 1 calc R U
C12 C 0.6362(3) 0.4676(8) 0.3995(3) 0.0264(8) Uani 1 1 d . .
C13 C 0.7045(3) 0.4765(7) 0.5109(3) 0.0294(9) Uani 1 1 d . .
C14 C 0.6217(4) 0.4801(7) 0.5778(3) 0.0309(10) Uani 1 1 d . .
H14 H 0.6424 0.4862 0.6552 0.037 Uiso 1 1 calc R U
C15 C 0.5003(3) 0.4730(7) 0.5080(3) 0.0275(8) Uani 1 1 d . .
C16 C 0.8870(4) 0.4950(11) 0.6519(4) 0.0527(17) Uani 1 1 d . .
H16A H 0.8525 0.6082 0.6828 0.079 Uiso 1 1 calc R U
H16B H 0.9791 0.5088 0.6644 0.079 Uiso 1 1 calc R U
H16C H 0.8672 0.3751 0.6871 0.079 Uiso 1 1 calc R U
C17 C 0.3825(3) 0.4732(7) 0.5419(3) 0.0295(8) Uani 1 1 d . .
C18 C 0.3664(4) 0.4710(8) 0.6472(3) 0.0321(9) Uani 1 1 d . .
H18 H 0.4317 0.4689 0.7125 0.039 Uiso 1 1 calc R U
C19 C 0.2354(4) 0.4723(8) 0.6398(3) 0.0351(10) Uani 1 1 d . .
H19 H 0.1955 0.4707 0.6991 0.042 Uiso 1 1 calc R U
C20 C 0.1760(4) 0.4765(8) 0.5312(4) 0.0378(11) Uani 1 1 d . .
H20 H 0.0870 0.4798 0.5019 0.045 Uiso 1 1 calc R U
N1 N 0.5177(3) 0.4494(7) 0.1404(2) 0.0257(6) Uani 1 1 d . .
H1 H 0.4517 0.4525 0.1694 0.031 Uiso 1 1 calc R U
N2 N 0.5087(3) 0.4672(6) 0.4031(2) 0.0262(7) Uani 1 1 d . .
H2 H 0.4439 0.4637 0.3459 0.031 Uiso 1 1 calc R U
N3 N 0.2656(3) 0.4750(7) 0.4723(3) 0.0345(8) Uani 1 1 d . .
H3 H 0.2504 0.4752 0.4005 0.041 Uiso 1 1 calc R U
O1 O 0.8314(2) 0.4847(6) 0.5363(2) 0.0380(8) Uani 1 1 d . .
Cl1 Cl 0.25990(8) 0.4457(2) 0.21844(7) 0.0370(3) Uani 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'
Cl Cl 0.3639 0.7018 '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
N1 C1 C2 108.5(3)
N1 C1 C9 122.5(3)
C2 C1 C9 129.0(3)
C7 C2 C1 107.3(3)
C7 C2 C3 124.8(3)
C1 C2 C3 127.9(3)
C2 C3 C4 110.1(3)
C2 C3 H3A 109.6
C4 C3 H3A 109.6
C2 C3 H3B 109.6
C4 C3 H3B 109.6
H3A C3 H3B 108.2
C5 C4 C3 112.4(4)
C5 C4 H4A 109.1
C3 C4 H4A 109.1
C5 C4 H4B 109.1
C3 C4 H4B 109.1
H4A C4 H4B 107.9
C4 C5 C6 111.8(4)
C4 C5 H5A 109.2
C6 C5 H5A 109.2
C4 C5 H5B 109.2
C6 C5 H5B 109.2
H5A C5 H5B 107.9
C7 C6 C10 112.6(4)
C7 C6 C5 108.5(3)
C10 C6 C5 111.9(4)
C7 C6 H6 107.9
C10 C6 H6 107.9
C5 C6 H6 107.9
C2 C7 C8 108.3(3)
C2 C7 C6 123.6(3)
C8 C7 C6 128.1(3)
N1 C8 C11 128.1(3)
N1 C8 C7 105.9(3)
C11 C8 C7 126.0(3)
C1 C9 H9A 109.5
C1 C9 H9B 109.5
H9A C9 H9B 109.5
C1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C6 C10 H10A 109.5
C6 C10 H10B 109.5
H10A C10 H10B 109.5
C6 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C8 134.9(3)
C12 C11 H11 112.6
C8 C11 H11 112.6
C11 C12 N2 129.9(3)
C11 C12 C13 125.3(3)
N2 C12 C13 104.8(3)
O1 C13 C14 129.8(4)
O1 C13 C12 120.1(3)
C14 C13 C12 110.0(3)
C13 C14 C15 105.7(3)
C13 C14 H14 127.1
C15 C14 H14 127.1
N2 C15 C14 110.1(3)
N2 C15 C17 124.2(3)
C14 C15 C17 125.7(3)
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N3 C17 C18 107.9(3)
N3 C17 C15 124.5(3)
C18 C17 C15 127.6(4)
C17 C18 C19 107.2(3)
C17 C18 H18 126.4
C19 C18 H18 126.4
C20 C19 C18 107.2(3)
C20 C19 H19 126.4
C18 C19 H19 126.4
N3 C20 C19 108.6(3)
N3 C20 H20 125.7
C19 C20 H20 125.7
C1 N1 C8 110.1(3)
C1 N1 H1 125.0
C8 N1 H1 125.0
C15 N2 C12 109.3(3)
C15 N2 H2 125.3
C12 N2 H2 125.3
C20 N3 C17 109.1(3)
C20 N3 H3 125.4
C17 N3 H3 125.4
C13 O1 C16 113.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.352(4)
C1 C2 1.401(5)
C1 C9 1.492(5)
C2 C7 1.383(5)
C2 C3 1.508(5)
C3 C4 1.530(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.528(7)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.542(6)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.501(5)
C6 C10 1.520(7)
C6 H6 1.0000
C7 C8 1.420(5)
C8 N1 1.388(4)
C8 C11 1.388(5)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.374(5)
C11 H11 0.9500
C12 N2 1.397(4)
C12 C13 1.425(5)
C13 O1 1.341(4)
C13 C14 1.372(5)
C14 C15 1.401(5)
C14 H14 0.9500
C15 N2 1.348(4)
C15 C17 1.443(5)
C16 O1 1.440(5)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 N3 1.362(5)
C17 C18 1.381(5)
C18 C19 1.404(5)
C18 H18 0.9500
C19 C20 1.368(6)
C19 H19 0.9500
C20 N3 1.358(5)
C20 H20 0.9500
N1 H1 0.8800
N2 H2 0.8800
N3 H3 0.8800
