#------------------------------------------------------------------------------
#$Date: 2019-11-04 10:21:17 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222465 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/38/4033890.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_4033890
loop_
_publ_author_name
'Wang, Pengzhi'
'Chau Nguyen, Khiem'
'Lindsey, Jonathan S.'
_publ_section_title
;
 Synthesis of the Ring C Pyrrole of Native Chlorophylls and
 Bacteriochlorophylls.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11286
_journal_page_last               11293
_journal_paper_doi               10.1021/acs.joc.9b01650
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C11.99 H11.96 I1.01 N O2 S'
_chemical_formula_weight         362.83
_chemical_name_common            Py-Ts-Me-I
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.3705(3)
_cell_length_b                   16.0873(7)
_cell_length_c                   25.9006(11)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.8710
_cell_measurement_theta_min      2.5328
_cell_volume                     2654.4(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            61299
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.53
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1413
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.837
_refine_diff_density_min         -1.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0450
_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)+20.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                2611
_reflns_number_total             3295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01650_si_003.cif
_cod_data_source_block           rds815
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4033890
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.21662(5) 0.83019(2) 0.06624(2) 0.02419(10) Uani d . . D 1.0 . .
S S1 0.22594(19) 0.86933(7) -0.15371(4) 0.0154(2) Uani d . . . 1.0 . .
O O1 0.4479(5) 0.8583(2) -0.15234(13) 0.0207(8) Uani d . . . 1.0 . .
O O2 0.1321(6) 0.9351(2) -0.18189(13) 0.0211(8) Uani d . . . 1.0 . .
N N1 0.1554(6) 0.8835(3) -0.09240(15) 0.0162(8) Uani d . . . 1.0 . .
C C1 0.2625(7) 0.8506(3) -0.05033(17) 0.0150(9) Uani d . . . 1.0 . .
H H1 0.398698 0.826537 -0.050651 0.018 Uiso calc U . R 1.0 . .
C C2 0.1341(7) 0.8597(3) -0.00838(18) 0.0166(10) Uani d . . D 1.0 . .
C C3 -0.0601(7) 0.8967(3) -0.02466(19) 0.0159(10) Uani d . . D 1.0 . .
C C4 -0.0432(8) 0.9095(3) -0.07625(19) 0.0195(11) Uani d . . . 1.0 . .
H H4 -0.148929 0.932438 -0.097834 0.023 Uiso calc U . R 1.0 . .
C C5 -0.2443(9) 0.9155(4) 0.0100(3) 0.0216(12) Uani d U P . 0.9853(18) A 1
H H5A -0.301064 0.8635 0.023906 0.032 Uiso calc U P R 0.9853(18) A 1
H H5B -0.353353 0.944227 -0.00983 0.032 Uiso calc U P R 0.9853(18) A 1
H H5C -0.198163 0.951126 0.038568 0.032 Uiso calc U P R 0.9853(18) A 1
C C6 0.1062(7) 0.7751(3) -0.17101(17) 0.0125(9) Uani d . . . 1.0 . .
C C7 0.2087(8) 0.7002(3) -0.16069(17) 0.0160(9) Uani d . . . 1.0 . .
H H7 0.3459 0.700403 -0.146302 0.019 Uiso calc U . R 1.0 . .
C C8 0.1100(8) 0.6262(3) -0.17147(18) 0.0180(10) Uani d . . . 1.0 . .
H H8 0.179337 0.575046 -0.164663 0.022 Uiso calc U . R 1.0 . .
C C9 -0.0927(8) 0.6260(3) -0.19248(17) 0.0174(10) Uani d . . . 1.0 . .
C C10 -0.1906(7) 0.7012(3) -0.20290(17) 0.0179(10) Uani d . . . 1.0 . .
H H10 -0.326836 0.701055 -0.217786 0.021 Uiso calc U . R 1.0 . .
C C11 -0.0951(7) 0.7762(3) -0.19219(17) 0.0166(10) Uani d . . . 1.0 . .
H H11 -0.164578 0.827228 -0.199068 0.02 Uiso calc U . R 1.0 . .
C C12 -0.2022(9) 0.5453(3) -0.2031(2) 0.0253(11) Uani d . . . 1.0 . .
H H12A -0.351068 0.55039 -0.194134 0.038 Uiso calc U . R 1.0 . .
H H12B -0.138175 0.501094 -0.182373 0.038 Uiso calc U . R 1.0 . .
H H12C -0.188936 0.531543 -0.239855 0.038 Uiso calc U . R 1.0 . .
I I2 -0.264(4) 0.9029(16) 0.0328(8) 0.016(8) Uani d U P D 0.0147(18) A 2
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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 121.6(2)
O2 S1 N1 106.0(2)
O1 S1 N1 105.1(2)
O2 S1 C6 109.3(2)
O1 S1 C6 109.3(2)
N1 S1 C6 104.1(2)
C1 N1 C4 108.9(4)
C1 N1 S1 124.3(3)
C4 N1 S1 124.8(3)
C2 C1 N1 106.8(4)
C2 C1 H1 126.6
N1 C1 H1 126.6
C1 C2 C3 109.0(4)
C1 C2 I1 124.6(4)
C3 C2 I1 126.3(3)
C4 C3 C2 106.5(4)
C4 C3 C5 128.2(5)
C2 C3 C5 125.3(4)
C4 C3 I2 141.8(9)
C2 C3 I2 111.4(9)
C3 C4 N1 108.7(4)
C3 C4 H4 125.6
N1 C4 H4 125.6
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C11 C6 C7 121.1(4)
C11 C6 S1 119.3(4)
C7 C6 S1 119.5(3)
C8 C7 C6 119.6(4)
C8 C7 H7 120.2
C6 C7 H7 120.2
C7 C8 C9 120.1(5)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 119.2(5)
C10 C9 C12 120.7(4)
C8 C9 C12 120.1(5)
C11 C10 C9 121.7(4)
C11 C10 H10 119.2
C9 C10 H10 119.2
C10 C11 C6 118.3(5)
C10 C11 H11 120.9
C6 C11 H11 120.9
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C2 2.058(5)
S1 O2 1.418(4)
S1 O1 1.425(4)
S1 N1 1.666(4)
S1 C6 1.755(5)
N1 C1 1.390(6)
N1 C4 1.397(6)
C1 C2 1.368(6)
C1 H1 0.95
C2 C3 1.436(7)
C3 C4 1.356(7)
C3 C5 1.509(7)
C3 I2 1.978(17)
C4 H4 0.95
C5 H5A 0.98
C5 H5B 0.98
C5 H5C 0.98
C6 C11 1.395(6)
C6 C7 1.396(6)
C7 C8 1.376(7)
C7 H7 0.95
C8 C9 1.401(7)
C8 H8 0.95
C9 C10 1.387(7)
C9 C12 1.500(7)
C10 C11 1.379(7)
C10 H10 0.95
C11 H11 0.95
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 N1 C1 -158.5(4)
O1 S1 N1 C1 -28.6(4)
C6 S1 N1 C1 86.3(4)
O2 S1 N1 C4 39.6(5)
O1 S1 N1 C4 169.5(4)
C6 S1 N1 C4 -75.6(4)
C4 N1 C1 C2 -2.5(5)
S1 N1 C1 C2 -166.8(4)
N1 C1 C2 C3 1.7(5)
N1 C1 C2 I1 -175.3(3)
C1 C2 C3 C4 -0.4(6)
I1 C2 C3 C4 176.6(4)
C1 C2 C3 C5 178.9(5)
I1 C2 C3 C5 -4.1(7)
C1 C2 C3 I2 175.1(8)
I1 C2 C3 I2 -7.9(9)
C2 C3 C4 N1 -1.2(6)
C5 C3 C4 N1 179.5(5)
I2 C3 C4 N1 -174.4(13)
C1 N1 C4 C3 2.3(6)
S1 N1 C4 C3 166.5(4)
O2 S1 C6 C11 -22.5(4)
O1 S1 C6 C11 -157.7(4)
N1 S1 C6 C11 90.4(4)
O2 S1 C6 C7 161.1(4)
O1 S1 C6 C7 25.9(4)
N1 S1 C6 C7 -86.0(4)
C11 C6 C7 C8 -0.1(7)
S1 C6 C7 C8 176.2(4)
C6 C7 C8 C9 -0.3(7)
C7 C8 C9 C10 0.9(7)
C7 C8 C9 C12 -178.6(4)
C8 C9 C10 C11 -1.3(7)
C12 C9 C10 C11 178.3(5)
C9 C10 C11 C6 0.9(7)
C7 C6 C11 C10 -0.2(7)
S1 C6 C11 C10 -176.5(3)
