#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/77/4037745.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_4037745
loop_
_publ_author_name
'Wang, Pengzhi'
'Lu, Futai'
'Lindsey, Jonathan S.'
_publ_section_title
;
 Use of the Nascent Isocyclic Ring to Anchor Assembly of the Full Skeleton
 of Model Chlorophylls
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02770
_journal_year                    2019
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_name_common            pyrrole-Ar
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 99.6754(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0874(10)
_cell_length_b                   7.3311(6)
_cell_length_c                   13.1798(12)
_cell_measurement_reflns_used    175
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      34.9142
_cell_measurement_theta_min      2.2672
_cell_volume                     1056.05(16)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_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 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27626
_diffrn_reflns_theta_full        35.02
_diffrn_reflns_theta_max         35.02
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         4649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0460
_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)+(0.0721P)²+0.2059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                3626
_reflns_number_total             4649
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02770_si_003.cif
_cod_data_source_block           rds726
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4037745
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_posn
_atom_site_occupancy
O O1 0.34308(6) 0.06917(10) 0.52485(5) 0.01970(14) Uani d . . 1
N N1 0.57211(7) 0.08555(10) 0.64502(6) 0.01543(14) Uani d . . 1
H H1 0.5751(12) 0.0259(18) 0.5851(10) 0.019 Uiso d U . 1
C C1 0.46813(7) 0.14228(11) 0.68030(6) 0.01342(14) Uani d . . 1
C C2 0.50593(8) 0.22853(11) 0.77464(6) 0.01562(15) Uani d . . 1
H H2 0.454295 0.282712 0.816881 0.019 Uiso calc U R 1
C C3 0.63432(8) 0.22062(13) 0.79577(7) 0.01899(17) Uani d . . 1
H H3 0.685571 0.268458 0.8548 0.023 Uiso calc U R 1
C C4 0.67218(8) 0.13000(13) 0.71441(7) 0.01867(17) Uani d . . 1
H H4 0.754534 0.103499 0.708328 0.022 Uiso calc U R 1
C C5 0.34985(8) 0.11504(11) 0.61639(6) 0.01385(14) Uani d . . 1
C C6 0.23547(7) 0.14555(11) 0.65927(6) 0.01295(14) Uani d . . 1
C C7 0.13168(8) 0.20257(11) 0.59128(6) 0.01471(15) Uani d . . 1
H H7 0.136304 0.219563 0.520578 0.018 Uiso calc U R 1
C C8 0.02169(8) 0.23476(11) 0.62584(6) 0.01494(15) Uani d . . 1
C C9 0.01770(8) 0.20747(11) 0.73012(6) 0.01528(15) Uani d . . 1
H H9 -0.056086 0.233008 0.755032 0.018 Uiso calc U R 1
C C10 0.11845(8) 0.14399(11) 0.79888(6) 0.01440(15) Uani d . . 1
C C11 0.22798(8) 0.11384(11) 0.76269(6) 0.01380(14) Uani d . . 1
H H11 0.297803 0.071587 0.808484 0.017 Uiso calc U R 1
C C12 -0.09092(8) 0.29336(14) 0.55260(7) 0.02075(17) Uani d . . 1
H H12A -0.1381 0.185417 0.5261 0.031 Uiso calc U R 1
H H12B -0.066606 0.361057 0.495175 0.031 Uiso calc U R 1
H H12C -0.141293 0.371708 0.588886 0.031 Uiso calc U R 1
C C13 0.10671(9) 0.10537(14) 0.90910(7) 0.02031(17) Uani d . . 1
H H13A 0.113904 0.219707 0.948174 0.03 Uiso calc U R 1
H H13B 0.171741 0.021506 0.939359 0.03 Uiso calc U R 1
H H13C 0.026832 0.049792 0.911431 0.03 Uiso calc U R 1
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
C4 N1 C1 109.67(7)
C4 N1 H1 123.9(8)
C1 N1 H1 126.4(8)
N1 C1 C2 107.13(7)
N1 C1 C5 119.29(7)
C2 C1 C5 133.46(8)
C1 C2 C3 107.49(7)
C1 C2 H2 126.3
C3 C2 H2 126.3
C4 C3 C2 107.16(8)
C4 C3 H3 126.4
C2 C3 H3 126.4
N1 C4 C3 108.53(8)
N1 C4 H4 125.7
C3 C4 H4 125.7
O1 C5 C1 120.20(7)
O1 C5 C6 119.52(7)
C1 C5 C6 120.27(7)
C7 C6 C11 119.79(7)
C7 C6 C5 117.59(7)
C11 C6 C5 122.58(7)
C8 C7 C6 120.86(7)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 118.17(8)
C7 C8 C12 121.06(8)
C9 C8 C12 120.76(8)
C10 C9 C8 122.19(8)
C10 C9 H9 118.9
C8 C9 H9 118.9
C9 C10 C11 118.61(7)
C9 C10 C13 119.97(8)
C11 C10 C13 121.40(8)
C10 C11 C6 120.30(7)
C10 C11 H11 119.9
C6 C11 H11 119.9
C8 C12 H12A 109.5
C8 C12 H12B 109.5
H12A C12 H12B 109.5
C8 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.2425(10)
N1 C4 1.3537(11)
N1 C1 1.3778(11)
N1 H1 0.908(13)
C1 C2 1.3951(11)
C1 C5 1.4484(12)
C2 C3 1.4051(13)
C2 H2 0.95
C3 C4 1.3852(13)
C3 H3 0.95
C4 H4 0.95
C5 C6 1.4895(11)
C6 C7 1.3984(11)
C6 C11 1.3989(11)
C7 C8 1.3918(12)
C7 H7 0.95
C8 C9 1.3969(12)
C8 C12 1.5066(12)
C9 C10 1.3947(12)
C9 H9 0.95
C10 C11 1.3949(11)
C10 C13 1.5070(12)
C11 H11 0.95
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
C13 H13A 0.98
C13 H13B 0.98
C13 H13C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 3_656 0.908(13) 1.962(13) 2.8091(10) 154.5(12)
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
C4 N1 C1 C2 1.15(10)
C4 N1 C1 C5 177.67(8)
N1 C1 C2 C3 -0.65(10)
C5 C1 C2 C3 -176.46(9)
C1 C2 C3 C4 -0.07(10)
C1 N1 C4 C3 -1.21(11)
C2 C3 C4 N1 0.78(11)
N1 C1 C5 O1 -11.72(12)
C2 C1 C5 O1 163.70(9)
N1 C1 C5 C6 169.57(7)
C2 C1 C5 C6 -15.02(14)
O1 C5 C6 C7 -28.39(11)
C1 C5 C6 C7 150.34(8)
O1 C5 C6 C11 149.54(8)
C1 C5 C6 C11 -31.74(12)
C11 C6 C7 C8 2.35(12)
C5 C6 C7 C8 -179.66(8)
C6 C7 C8 C9 -0.38(12)
C6 C7 C8 C12 -179.03(8)
C7 C8 C9 C10 -2.13(13)
C12 C8 C9 C10 176.53(8)
C8 C9 C10 C11 2.58(12)
C8 C9 C10 C13 -176.03(8)
C9 C10 C11 C6 -0.52(12)
C13 C10 C11 C6 178.06(8)
C7 C6 C11 C10 -1.89(12)
C5 C6 C11 C10 -179.77(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 57894307
