#------------------------------------------------------------------------------
#$Date: 2019-09-18 16:56:41 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200355.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_7200355
loop_
_publ_author_name
'Jenkins, Samir'
'Incarvito, Christopher D.'
'Parr, Jonathan'
'Wasserman, Harry H.'
_publ_section_title
;
 Structural studies of C-ring substituted unnatural analogues of prodigiosin
;
_journal_coden_ASTM              CRECF4
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              242
_journal_page_last               245
_journal_paper_doi               10.1039/b813351d
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C16 H17 N3 O'
_chemical_formula_weight         267.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 93.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.048(3)
_cell_length_b                   17.811(4)
_cell_length_c                   9.3594(19)
_cell_measurement_temperature    173(2)
_cell_volume                     2836.3(10)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '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  0.0838
_diffrn_reflns_av_sigmaI/netI    0.1842
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11426
_diffrn_reflns_theta_full        28.98
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         7352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.2305
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.2041
_reflns_number_gt                2911
_reflns_number_total             7352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B813351D.txt
_cod_data_source_block           sj03
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_cell_volume        2836.2(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7200355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.00746(12) 0.42193(14) 0.2855(2) 0.0529(7) Uani 1 1 d . . .
N1 N 0.69398(14) 0.57234(15) 0.3119(3) 0.0389(7) Uani 1 1 d . . .
H1 H 0.685(2) 0.548(2) 0.409(5) 0.090(14) Uiso 1 1 d . . .
N2 N 0.82621(13) 0.48433(14) 0.4183(3) 0.0380(7) Uani 1 1 d . . .
N3 N 0.81709(15) 0.42142(16) 0.7134(3) 0.0372(7) Uani 1 1 d . . .
H3 H 0.7848(19) 0.4503(18) 0.663(4) 0.049(11) Uiso 1 1 d . . .
C1 C 0.64472(18) 0.62015(18) 0.2386(4) 0.0399(8) Uani 1 1 d . . .
H1A H 0.5958 0.6374 0.2694 0.048 Uiso 1 1 calc R . .
C2 C 0.67595(18) 0.63964(18) 0.1141(4) 0.0444(9) Uani 1 1 d . . .
H2A H 0.6530 0.6722 0.0429 0.053 Uiso 1 1 calc R . .
C3 C 0.74810(18) 0.60299(18) 0.1102(4) 0.0421(9) Uani 1 1 d . . .
H3A H 0.7834 0.6063 0.0359 0.051 Uiso 1 1 calc R . .
C4 C 0.75874(17) 0.56119(16) 0.2335(4) 0.0362(8) Uani 1 1 d . . .
C5 C 0.82430(17) 0.51547(17) 0.2875(4) 0.0386(8) Uani 1 1 d . . .
C6 C 0.89213(17) 0.49887(18) 0.2106(4) 0.0404(8) Uani 1 1 d . . .
H6A H 0.9029 0.5150 0.1171 0.048 Uiso 1 1 calc R . .
C7 C 0.93781(18) 0.45498(19) 0.3006(4) 0.0421(8) Uani 1 1 d . . .
C8 C 0.89783(17) 0.44553(18) 0.4319(4) 0.0402(8) Uani 1 1 d . . .
C9 C 0.92367(18) 0.40464(19) 0.5458(4) 0.0444(9) Uani 1 1 d . . .
H9A H 0.9727 0.3804 0.5367 0.053 Uiso 1 1 calc R . .
C10 C 0.88880(17) 0.39198(18) 0.6785(4) 0.0395(8) Uani 1 1 d . . .
C11 C 0.91792(17) 0.35031(18) 0.7962(4) 0.0412(8) Uani 1 1 d . . .
C12 C 0.86314(18) 0.35628(18) 0.9010(4) 0.0420(8) Uani 1 1 d . . .
H12A H 0.8678 0.3340 0.9933 0.050 Uiso 1 1 calc R . .
C13 C 0.80132(18) 0.39997(17) 0.8476(4) 0.0380(8) Uani 1 1 d . . .
C14 C 1.04196(19) 0.4366(2) 0.1526(4) 0.0499(9) Uani 1 1 d . . .
H14A H 1.0922 0.4100 0.1509 0.075 Uiso 1 1 calc R . .
H14B H 1.0508 0.4907 0.1430 0.075 Uiso 1 1 calc R . .
H14C H 1.0064 0.4192 0.0731 0.075 Uiso 1 1 calc R . .
C15 C 0.9930(2) 0.3066(2) 0.8070(4) 0.0606(11) Uani 1 1 d . . .
H15A H 0.9994 0.2826 0.9013 0.091 Uiso 1 1 calc R . .
H15B H 1.0373 0.3405 0.7944 0.091 Uiso 1 1 calc R . .
H15C H 0.9914 0.2679 0.7323 0.091 Uiso 1 1 calc R . .
C16 C 0.72824(18) 0.42272(19) 0.9139(4) 0.0466(9) Uani 1 1 d . . .
H16A H 0.6963 0.4539 0.8466 0.070 Uiso 1 1 calc R . .
H16B H 0.7417 0.4514 1.0014 0.070 Uiso 1 1 calc R . .
H16C H 0.6984 0.3779 0.9377 0.070 Uiso 1 1 calc R . .
O1' O 0.48268(11) 0.50151(11) 0.7643(2) 0.0413(6) Uani 1 1 d . . .
N1' N 0.79650(14) 0.61618(16) 0.6053(3) 0.0416(7) Uani 1 1 d . . .
H1' H 0.8061(19) 0.5787(19) 0.547(4) 0.051(11) Uiso 1 1 d . . .
N2' N 0.66665(13) 0.51275(14) 0.5997(3) 0.0347(6) Uani 1 1 d . . .
N3' N 0.68064(15) 0.37301(15) 0.4216(3) 0.0391(7) Uani 1 1 d . . .
H3' H 0.714(2) 0.412(2) 0.442(4) 0.059(11) Uiso 1 1 d . . .
C1' C 0.84658(18) 0.67507(18) 0.6262(4) 0.0470(9) Uani 1 1 d . . .
H1'A H 0.8953 0.6812 0.5836 0.056 Uiso 1 1 calc R . .
C2' C 0.81494(19) 0.7238(2) 0.7185(4) 0.0535(10) Uani 1 1 d . . .
H2'A H 0.8377 0.7697 0.7521 0.064 Uiso 1 1 calc R . .
C3' C 0.74323(19) 0.69433(17) 0.7551(4) 0.0445(9) Uani 1 1 d . . .
H3'A H 0.7085 0.7164 0.8186 0.053 Uiso 1 1 calc R . .
C4' C 0.73157(16) 0.62741(17) 0.6828(3) 0.0366(8) Uani 1 1 d . . .
C5' C 0.66726(16) 0.57541(17) 0.6789(3) 0.0355(8) Uani 1 1 d . . .
C6' C 0.59754(16) 0.58453(18) 0.7559(3) 0.0366(8) Uani 1 1 d . . .
H6'A H 0.5855 0.6249 0.8173 0.044 Uiso 1 1 calc R . .
C7' C 0.55276(16) 0.52376(17) 0.7228(3) 0.0346(7) Uani 1 1 d . . .
C8' C 0.59538(16) 0.47761(17) 0.6244(3) 0.0346(8) Uani 1 1 d . . .
C9' C 0.57027(17) 0.41086(17) 0.5679(3) 0.0362(8) Uani 1 1 d . . .
H9'A H 0.5199 0.3951 0.5940 0.043 Uiso 1 1 calc R . .
C10' C 0.60791(17) 0.36146(17) 0.4761(3) 0.0359(8) Uani 1 1 d . . .
C11' C 0.57990(18) 0.29261(17) 0.4209(3) 0.0396(8) Uani 1 1 d . . .
C12' C 0.63619(19) 0.26519(19) 0.3315(4) 0.0450(9) Uani 1 1 d . . .
H12B H 0.6323 0.2200 0.2777 0.054 Uiso 1 1 calc R . .
C13' C 0.69836(18) 0.31514(18) 0.3349(4) 0.0397(8) Uani 1 1 d . . .
C14' C 0.44534(18) 0.55214(19) 0.8583(4) 0.0444(9) Uani 1 1 d . . .
H14D H 0.3947 0.5312 0.8825 0.067 Uiso 1 1 calc R . .
H14E H 0.4368 0.6007 0.8106 0.067 Uiso 1 1 calc R . .
H14F H 0.4790 0.5591 0.9461 0.067 Uiso 1 1 calc R . .
C15' C 0.50370(19) 0.25641(19) 0.4526(4) 0.0556(10) Uani 1 1 d . . .
H15D H 0.4977 0.2091 0.3996 0.083 Uiso 1 1 calc R . .
H15E H 0.4601 0.2901 0.4236 0.083 Uiso 1 1 calc R . .
H15F H 0.5033 0.2463 0.5555 0.083 Uiso 1 1 calc R . .
C16' C 0.7734(2) 0.3112(2) 0.2629(4) 0.0547(10) Uani 1 1 d . . .
H16D H 0.8048 0.3561 0.2865 0.082 Uiso 1 1 calc R . .
H16E H 0.7623 0.3084 0.1590 0.082 Uiso 1 1 calc R . .
H16F H 0.8027 0.2664 0.2957 0.082 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'
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
C7 O1 C14 115.2(3) . . ?
H1 N1 C1 126(2) . . ?
H1 N1 C4 125(2) . . ?
C1 N1 C4 108.3(3) . . ?
C5 N2 C8 104.9(2) . . ?
H3 N3 C13 121(2) . . ?
H3 N3 C10 129(2) . . ?
C13 N3 C10 109.9(3) . . ?
N1 C1 C2 109.4(3) . . ?
C1 C2 C3 107.3(3) . . ?
C4 C3 C2 107.5(3) . . ?
N1 C4 C3 107.5(3) . . ?
N1 C4 C5 121.5(3) . . ?
C3 C4 C5 130.9(3) . . ?
N2 C5 C6 113.5(3) . . ?
N2 C5 C4 121.6(3) . . ?
C6 C5 C4 124.8(3) . . ?
C7 C6 C5 104.9(3) . . ?
O1 C7 C6 131.6(3) . . ?
O1 C7 C8 120.3(3) . . ?
C6 C7 C8 108.1(3) . . ?
C9 C8 N2 125.5(3) . . ?
C9 C8 C7 125.9(3) . . ?
N2 C8 C7 108.6(3) . . ?
C8 C9 C10 130.0(3) . . ?
N3 C10 C11 106.9(3) . . ?
N3 C10 C9 124.5(3) . . ?
C11 C10 C9 128.6(3) . . ?
C10 C11 C12 107.1(3) . . ?
C10 C11 C15 126.3(3) . . ?
C12 C11 C15 126.7(3) . . ?
C13 C12 C11 108.5(3) . . ?
N3 C13 C12 107.7(3) . . ?
N3 C13 C16 122.1(3) . . ?
C12 C13 C16 130.2(3) . . ?
C7' O1' C14' 115.4(2) . . ?
H1' N1' C1' 122(2) . . ?
H1' N1' C4' 128(2) . . ?
C1' N1' C4' 109.3(3) . . ?
C5' N2' C8' 104.9(2) . . ?
H3' N3' C13' 123(2) . . ?
H3' N3' C10' 127(2) . . ?
C13' N3' C10' 110.2(3) . . ?
N1' C1' C2' 108.3(3) . . ?
C1' C2' C3' 107.8(3) . . ?
C4' C3' C2' 107.8(3) . . ?
N1' C4' C3' 106.8(3) . . ?
N1' C4' C5' 122.1(3) . . ?
C3' C4' C5' 131.1(3) . . ?
N2' C5' C4' 122.1(3) . . ?
N2' C5' C6' 113.2(3) . . ?
C4' C5' C6' 124.7(3) . . ?
C7' C6' C5' 105.5(3) . . ?
O1' C7' C6' 132.3(3) . . ?
O1' C7' C8' 120.3(3) . . ?
C6' C7' C8' 107.4(3) . . ?
C9' C8' N2' 125.6(3) . . ?
C9' C8' C7' 125.5(3) . . ?
N2' C8' C7' 108.9(3) . . ?
C8' C9' C10' 129.6(3) . . ?
N3' C10' C11' 106.6(3) . . ?
N3' C10' C9' 125.7(3) . . ?
C11' C10' C9' 127.7(3) . . ?
C12' C11' C10' 107.1(3) . . ?
C12' C11' C15' 127.2(3) . . ?
C10' C11' C15' 125.7(3) . . ?
C13' C12' C11' 108.4(3) . . ?
N3' C13' C12' 107.6(3) . . ?
N3' C13' C16' 122.5(3) . . ?
C12' C13' C16' 129.8(3) . . ?
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
O1 C7 1.341(4) . ?
O1 C14 1.432(4) . ?
N1 H1 1.03(4) . ?
N1 C1 1.352(4) . ?
N1 C4 1.378(4) . ?
N2 C5 1.343(4) . ?
N2 C8 1.402(4) . ?
N3 H3 0.87(3) . ?
N3 C13 1.356(4) . ?
N3 C10 1.388(4) . ?
C1 C2 1.356(4) . ?
C2 C3 1.395(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.448(4) . ?
C5 C6 1.431(4) . ?
C6 C7 1.358(4) . ?
C7 C8 1.452(4) . ?
C8 C9 1.342(4) . ?
C9 C10 1.428(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.400(4) . ?
C11 C15 1.496(4) . ?
C12 C13 1.378(4) . ?
C13 C16 1.483(4) . ?
O1' C7' 1.339(3) . ?
O1' C14' 1.437(3) . ?
N1' H1' 0.88(3) . ?
N1' C1' 1.359(4) . ?
N1' C4' 1.376(4) . ?
N2' C5' 1.339(4) . ?
N2' C8' 1.399(3) . ?
N3' H3' 0.91(4) . ?
N3' C13' 1.358(4) . ?
N3' C10' 1.386(4) . ?
C1' C2' 1.360(5) . ?
C2' C3' 1.393(4) . ?
C3' C4' 1.379(4) . ?
C4' C5' 1.434(4) . ?
C5' C6' 1.438(4) . ?
C6' C7' 1.349(4) . ?
C7' C8' 1.462(4) . ?
C8' C9' 1.360(4) . ?
C9' C10' 1.412(4) . ?
C10' C11' 1.403(4) . ?
C11' C12' 1.400(4) . ?
C11' C15' 1.497(4) . ?
C12' C13' 1.383(4) . ?
C13' C16' 1.485(4) . ?
