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#$Date: 2020-05-28 02:24:00 +0300 (Thu, 28 May 2020) $
#$Revision: 252402 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038418.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_4038418
loop_
_publ_author_name
'Kielmann, Marc'
'Flanagan, Keith J.'
'Senge, Mathias O.'
_publ_section_title
;
 Targeted Synthesis of Regioisomerically Pure Dodecasubstituted Type I
 Porphyrins through the Exploitation of Peri-interactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00798
_journal_year                    2020
_chemical_formula_moiety         'C9 H13 N O'
_chemical_formula_sum            'C9 H13 N O'
_chemical_formula_weight         151.20
_chemical_name_systematic        3-acetyl-4-isopropylpyrrole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.910(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0803(8)
_cell_length_b                   6.7468(6)
_cell_length_c                   14.6471(12)
_cell_measurement_reflns_used    4775
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.24
_cell_volume                     896.83(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016) '
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18366
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0627 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.8832. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Liquid diffusion layering DCM with hexane'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0449
_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)+(0.0452P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1559
_reflns_number_total             2065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00798_si_002.cif
_cod_data_source_block           kjf234
_cod_database_code               4038418
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), N1(H1A)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_olex2_exptl_crystal_mounting_method
'Mounted on a MiTiGen micromount using oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73799(15) 0.3169(2) 0.23551(9) 0.0226(3) Uani 1 1 d . . . . .
H1 H 0.8206 0.3455 0.1996 0.027 Uiso 1 1 calc R . . . .
C2 C 0.73520(15) 0.3311(2) 0.32867(9) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.58803(15) 0.2754(2) 0.35283(9) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.51120(16) 0.2301(2) 0.27171(9) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.4113 0.1888 0.2664 0.027 Uiso 1 1 calc R . . . .
C5 C 0.86327(15) 0.3832(2) 0.39224(10) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.8248 0.4648 0.4432 0.027 Uiso 1 1 calc R . . . .
C6 C 0.93200(17) 0.1953(2) 0.43371(11) 0.0296(4) Uani 1 1 d . . . . .
H6A H 0.8571 0.1219 0.4666 0.044 Uiso 1 1 calc GR . . . .
H6B H 1.0131 0.2316 0.4762 0.044 Uiso 1 1 calc GR . . . .
H6C H 0.9697 0.1120 0.3849 0.044 Uiso 1 1 calc GR . . . .
C7 C 0.97955(17) 0.5057(3) 0.34458(11) 0.0326(4) Uani 1 1 d . . . . .
H7A H 1.0203 0.4278 0.2949 0.049 Uiso 1 1 calc GR . . . .
H7B H 1.0587 0.5411 0.3887 0.049 Uiso 1 1 calc GR . . . .
H7C H 0.9342 0.6267 0.3196 0.049 Uiso 1 1 calc GR . . . .
C8 C 0.52738(16) 0.2666(2) 0.44310(9) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.36590(16) 0.2211(2) 0.45077(10) 0.0276(3) Uani 1 1 d . . . . .
H9A H 0.3075 0.3277 0.4221 0.041 Uiso 1 1 calc GR . . . .
H9B H 0.3421 0.2106 0.5154 0.041 Uiso 1 1 calc GR . . . .
H9C H 0.3431 0.0955 0.4198 0.041 Uiso 1 1 calc GR . . . .
N1 N 0.60242(13) 0.25461(18) 0.20210(8) 0.0236(3) Uani 1 1 d . . . . .
H1A H 0.5789 0.2340 0.1441 0.028 Uiso 1 1 calc R . . . .
O1 O 0.60432(11) 0.29639(16) 0.51279(6) 0.0256(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 0.0033 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
C2 C1 H1 125.4 . . ?
C2 C1 N1 109.27(12) . . ?
N1 C1 H1 125.4 . . ?
C1 C2 C3 105.91(12) . . ?
C1 C2 C5 126.34(13) . . ?
C3 C2 C5 127.66(12) . . ?
C2 C3 C8 128.09(12) . . ?
C4 C3 C2 106.84(12) . . ?
C4 C3 C8 125.06(13) . . ?
C3 C4 H4 125.8 . . ?
N1 C4 C3 108.45(13) . . ?
N1 C4 H4 125.8 . . ?
C2 C5 H5 107.9 . . ?
C2 C5 C6 110.37(12) . . ?
C2 C5 C7 112.01(12) . . ?
C6 C5 H5 107.9 . . ?
C7 C5 H5 107.9 . . ?
C7 C5 C6 110.53(12) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 C9 118.47(12) . . ?
O1 C8 C3 121.71(13) . . ?
O1 C8 C9 119.82(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 H1A 125.2 . . ?
C4 N1 C1 109.53(12) . . ?
C4 N1 H1A 125.2 . . ?
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
C1 H1 0.9500 . ?
C1 C2 1.3690(19) . ?
C1 N1 1.3754(18) . ?
C2 C3 1.4435(19) . ?
C2 C5 1.5070(19) . ?
C3 C4 1.3916(19) . ?
C3 C8 1.4504(19) . ?
C4 H4 0.9500 . ?
C4 N1 1.3451(18) . ?
C5 H5 1.0000 . ?
C5 C6 1.530(2) . ?
C5 C7 1.528(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.506(2) . ?
C8 O1 1.2340(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1 H1A 0.8800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.88 1.96 2.7947(15) 159.0 4_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.23(16) . . . . ?
C1 C2 C3 C8 -179.72(14) . . . . ?
C1 C2 C5 C6 -98.41(17) . . . . ?
C1 C2 C5 C7 25.2(2) . . . . ?
C2 C1 N1 C4 0.64(16) . . . . ?
C2 C3 C4 N1 0.15(16) . . . . ?
C2 C3 C8 C9 174.72(14) . . . . ?
C2 C3 C8 O1 -4.8(2) . . . . ?
C3 C2 C5 C6 77.79(18) . . . . ?
C3 C2 C5 C7 -158.60(14) . . . . ?
C3 C4 N1 C1 -0.48(16) . . . . ?
C4 C3 C8 C9 -5.2(2) . . . . ?
C4 C3 C8 O1 175.23(14) . . . . ?
C5 C2 C3 C4 -176.59(14) . . . . ?
C5 C2 C3 C8 3.5(2) . . . . ?
C8 C3 C4 N1 -179.90(13) . . . . ?
N1 C1 C2 C3 -0.52(16) . . . . ?
N1 C1 C2 C5 176.36(13) . . . . ?
