#------------------------------------------------------------------------------
#$Date: 2019-09-18 16:56:41 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200354.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_7200354
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 H18 Cl N3 O'
_chemical_formula_weight         303.78
_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                 97.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.751(2)
_cell_length_b                   9.5910(19)
_cell_length_c                   16.301(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1512.2(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.1592
_diffrn_reflns_av_sigmaI/netI    0.2347
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5864
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9390
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.2360
_refine_ls_R_factor_gt           0.0846
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.2297
_reflns_number_gt                1314
_reflns_number_total             3298
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B813351D.txt
_cod_data_source_block           sj01
_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_sg_symbol_H-M      P2(1)/c
_cod_database_code               7200354
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
Cl1 Cl 0.80382(15) 0.10497(16) 0.20465(8) 0.0364(5) Uani 1 1 d . . .
O1 O 0.7359(4) -0.0537(4) -0.1952(2) 0.0333(10) Uani 1 1 d . . .
N1 N 0.9992(5) 0.2711(5) 0.0992(3) 0.0336(12) Uani 1 1 d . . .
H1 H 0.949(6) 0.214(6) 0.137(3) 0.046(18) Uiso 1 1 d . . .
N2 N 0.8125(4) 0.0652(4) 0.0094(3) 0.0254(11) Uani 1 1 d . . .
H2 H 0.801(6) 0.068(6) 0.065(4) 0.047(19) Uiso 1 1 d . . .
N3 N 0.6067(5) -0.1224(5) 0.1101(3) 0.0274(11) Uani 1 1 d . . .
H3 H 0.662(7) -0.058(8) 0.126(4) 0.07(3) Uiso 1 1 d . . .
C1 C 1.0968(6) 0.3704(6) 0.1205(4) 0.0399(16) Uani 1 1 d . . .
H1A H 1.1214 0.4080 0.1743 0.048 Uiso 1 1 calc R . .
C2 C 1.1538(6) 0.4070(7) 0.0503(4) 0.0454(17) Uani 1 1 d . . .
H2A H 1.2247 0.4741 0.0474 0.055 Uiso 1 1 calc R . .
C3 C 1.0900(6) 0.3294(7) -0.0153(4) 0.0388(16) Uani 1 1 d . . .
H3A H 1.1094 0.3335 -0.0709 0.047 Uiso 1 1 calc R . .
C4 C 0.9925(6) 0.2445(6) 0.0150(3) 0.0287(13) Uani 1 1 d . . .
C5 C 0.9016(5) 0.1457(6) -0.0280(3) 0.0275(13) Uani 1 1 d . . .
C6 C 0.8881(5) 0.1120(6) -0.1125(3) 0.0288(13) Uani 1 1 d . . .
H6A H 0.9386 0.1515 -0.1529 0.035 Uiso 1 1 calc R . .
C7 C 0.7890(5) 0.0121(6) -0.1253(3) 0.0262(13) Uani 1 1 d . . .
C8 C 0.7369(5) -0.0219(6) -0.0499(3) 0.0254(13) Uani 1 1 d . . .
C9 C 0.6386(5) -0.1169(6) -0.0393(3) 0.0292(13) Uani 1 1 d . . .
H9A H 0.6023 -0.1606 -0.0897 0.035 Uiso 1 1 calc R . .
C10 C 0.5769(5) -0.1669(6) 0.0285(3) 0.0249(13) Uani 1 1 d . . .
C11 C 0.4758(6) -0.2686(5) 0.0274(3) 0.0258(13) Uani 1 1 d . . .
C12 C 0.4448(6) -0.2822(6) 0.1082(3) 0.0314(14) Uani 1 1 d . . .
H12A H 0.3781 -0.3440 0.1257 0.038 Uiso 1 1 calc R . .
C13 C 0.5258(5) -0.1922(6) 0.1583(3) 0.0264(13) Uani 1 1 d . . .
C14 C 0.7970(6) -0.0190(7) -0.2684(3) 0.0407(17) Uani 1 1 d . . .
H14A H 0.7513 -0.0723 -0.3154 0.061 Uiso 1 1 calc R . .
H14B H 0.8957 -0.0422 -0.2599 0.061 Uiso 1 1 calc R . .
H14C H 0.7857 0.0809 -0.2797 0.061 Uiso 1 1 calc R . .
C15 C 0.4116(6) -0.3453(6) -0.0483(3) 0.0369(16) Uani 1 1 d . . .
H15A H 0.3428 -0.4115 -0.0329 0.055 Uiso 1 1 calc R . .
H15B H 0.4836 -0.3959 -0.0729 0.055 Uiso 1 1 calc R . .
H15C H 0.3667 -0.2784 -0.0885 0.055 Uiso 1 1 calc R . .
C16 C 0.5321(6) -0.1654(6) 0.2485(3) 0.0365(16) Uani 1 1 d . . .
H16A H 0.6023 -0.0943 0.2651 0.055 Uiso 1 1 calc R . .
H16B H 0.5563 -0.2518 0.2791 0.055 Uiso 1 1 calc R . .
H16C H 0.4418 -0.1324 0.2609 0.055 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'
Cl Cl 0.1484 0.1585 '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 116.0(4) . . ?
H1 N1 C1 128(3) . . ?
H1 N1 C4 123(3) . . ?
C1 N1 C4 109.0(5) . . ?
H2 N2 C5 126(4) . . ?
H2 N2 C8 125(4) . . ?
C5 N2 C8 109.7(5) . . ?
H3 N3 C13 125(5) . . ?
H3 N3 C10 125(5) . . ?
C13 N3 C10 109.6(5) . . ?
N1 C1 C2 108.0(5) . . ?
C1 C2 C3 108.4(6) . . ?
C2 C3 C4 107.6(5) . . ?
C3 C4 N1 107.1(5) . . ?
C3 C4 C5 129.0(5) . . ?
N1 C4 C5 123.9(5) . . ?
N2 C5 C6 108.8(5) . . ?
N2 C5 C4 123.5(5) . . ?
C6 C5 C4 127.7(5) . . ?
C7 C6 C5 106.8(4) . . ?
O1 C7 C6 130.5(5) . . ?
O1 C7 C8 118.8(5) . . ?
C6 C7 C8 110.7(4) . . ?
C9 C8 N2 129.0(5) . . ?
C9 C8 C7 126.9(5) . . ?
N2 C8 C7 104.0(5) . . ?
C8 C9 C10 135.3(5) . . ?
C11 C10 N3 106.9(4) . . ?
C11 C10 C9 127.2(5) . . ?
N3 C10 C9 126.0(5) . . ?
C10 C11 C12 107.0(5) . . ?
C10 C11 C15 125.2(5) . . ?
C12 C11 C15 127.8(5) . . ?
C13 C12 C11 109.1(5) . . ?
N3 C13 C12 107.5(5) . . ?
N3 C13 C16 122.2(5) . . ?
C12 C13 C16 130.4(5) . . ?
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 1.347(6) . ?
O1 C14 1.439(6) . ?
N1 H1 0.99(6) . ?
N1 C1 1.360(7) . ?
N1 C4 1.390(7) . ?
N2 H2 0.92(6) . ?
N2 C5 1.362(7) . ?
N2 C8 1.412(7) . ?
N3 H3 0.84(7) . ?
N3 C13 1.357(7) . ?
N3 C10 1.393(7) . ?
C1 C2 1.379(8) . ?
C2 C3 1.383(8) . ?
C3 C4 1.389(8) . ?
C4 C5 1.420(7) . ?
C5 C6 1.405(7) . ?
C6 C7 1.359(7) . ?
C7 C8 1.425(7) . ?
C8 C9 1.350(7) . ?
C9 C10 1.407(7) . ?
C10 C11 1.385(7) . ?
C11 C12 1.394(7) . ?
C11 C15 1.504(7) . ?
C12 C13 1.368(7) . ?
C13 C16 1.487(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653545
