#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/54/7125461.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_7125461
loop_
_publ_author_name
'Pérollier, Céline'
'Pécaut, Jacques'
'Ramasseul, René'
'Marchon, Jean-Claude'
'Bau, Robert'
_publ_section_title
;
 High-yield synthesis of a chiroporphyrin by hydrogen bond-directed
 cyclisation
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1597
_journal_paper_doi               10.1039/a904134f
_journal_year                    1999
_chemical_formula_sum            'C20 H32 N2 O3'
_chemical_formula_weight         348.48
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.861(2)
_cell_length_b                   20.595(3)
_cell_length_c                   8.948(2)
_cell_measurement_temperature    163
_cell_volume                     2001.5(6)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1574
_diffrn_reflns_theta_max         50.72
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.615
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(180)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.187
_refine_ls_goodness_of_fit_obs   1.929
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.305
_refine_ls_restrained_S_obs      1.929
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_obs          0.0608
_refine_ls_shift/esd_max         -0.027
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2659P)²+9.7118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1882
_refine_ls_wR_factor_obs         0.1553
_reflns_number_observed          1287
_reflns_number_total             1425
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904134f.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.2659P)^2^+9.7118P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. A new data item '_refine_ls_weighting_details' was
created with the value set to
'w=1/[\s^2^(Fo^2^)+(0.2659P)^2^+9.7118P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7125461
loop_
_symmetry_equiv_pos_as_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'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
C1 C -0.0310(11) 0.0243(6) 0.0584(18) 0.036(4) Uani 1 d
C2 C 0.1008(12) 0.0381(7) 0.1098(21) 0.043(4) Uani 1 d
C3 C 0.0784(12) -0.0020(7) -0.0269(21) 0.046(5) Uani 1 d
C4 C 0.0966(15) -0.0741(7) -0.0113(27) 0.068(6) Uani 1 d
C5 C 0.1096(14) 0.0246(8) -0.1770(21) 0.057(5) Uani 1 d
C6 C 0.1547(13) 0.1031(8) 0.1059(24) 0.057(5) Uani 1 d
O7 O 0.2045(12) 0.1271(7) 0.2120(19) 0.089(4) Uani 1 d
C8 C -0.1088(11) 0.0780(6) 0.0033(18) 0.029(4) Uani 1 d
O9 O -0.0671(7) 0.1276(4) -0.0532(11) 0.040(3) Uani 1 d
N10 N -0.2339(9) 0.0702(4) 0.0212(13) 0.025(3) Uani 1 d
C11 C -0.2855(11) 0.0147(6) 0.0921(22) 0.028(4) Uani 1 d
O12 O -0.3256(9) 0.0188(4) 0.2209(14) 0.038(3) Uani 1 d
N13 N -0.2916(9) -0.0376(5) 0.0076(14) 0.030(3) Uani 1 d
C14 C -0.3472(12) -0.0986(6) 0.0572(17) 0.035(4) Uani 1 d
C15 C -0.4575(15) -0.1135(8) -0.0410(24) 0.071(6) Uani 1 d
C16 C -0.5167(22) -0.1771(10) 0.0088(32) 0.107(9) Uani 1 d
C17 C -0.4269(28) -0.2320(8) 0.0067(29) 0.104(9) Uani 1 d
C18 C -0.3184(18) -0.2163(7) 0.1075(24) 0.068(6) Uani 1 d
C19 C -0.2570(14) -0.1535(7) 0.0565(20) 0.051(5) Uani 1 d
C20 C -0.3170(11) 0.1260(6) -0.0133(17) 0.031(4) Uani 1 d
C21 C -0.3279(13) 0.1724(6) 0.1184(18) 0.042(4) Uani 1 d
C22 C -0.4068(15) 0.2292(7) 0.0750(21) 0.054(5) Uani 1 d
C23 C -0.5342(13) 0.2081(8) 0.0192(25) 0.062(5) Uani 1 d
C24 C -0.5206(14) 0.1614(7) -0.1079(22) 0.053(5) Uani 1 d
C25 C -0.4420(12) 0.1025(7) -0.0646(19) 0.043(4) Uani 1 d
H1 H -0.0755 -0.0086 0.1175 0.042 Uiso 1 d
H2 H 0.1298 0.0127 0.1940 0.060 Uiso 1 d
H3 H 0.0250 -0.0978 -0.0496 0.080 Uiso 1 d
H4 H 0.1092 -0.0873 0.0883 0.080 Uiso 1 d
H5 H 0.1660 -0.0901 -0.0706 0.080 Uiso 1 d
H6 H 0.1753 0.0000 -0.2251 0.072 Uiso 1 d
H7 H 0.1365 0.0690 -0.1735 0.072 Uiso 1 d
H8 H 0.0400 0.0227 -0.2441 0.072 Uiso 1 d
H9 H 0.1503 0.1291 0.0089 0.097 Uiso 1 d
H10 H -0.2555 -0.0359 -0.0898 0.097 Uiso 1 d
H11 H -0.3763 -0.0943 0.1594 0.053 Uiso 1 d
H12 H -0.4284 -0.1171 -0.1451 0.092 Uiso 1 d
H13 H -0.5129 -0.0768 -0.0407 0.092 Uiso 1 d
H14 H -0.5880 -0.1879 -0.0536 0.148 Uiso 1 d
H15 H -0.5515 -0.1715 0.1097 0.148 Uiso 1 d
H16 H -0.3970 -0.2376 -0.0903 0.137 Uiso 1 d
H17 H -0.4650 -0.2712 0.0412 0.137 Uiso 1 d
H18 H -0.2609 -0.2522 0.1086 0.093 Uiso 1 d
H19 H -0.3466 -0.2117 0.2111 0.093 Uiso 1 d
H20 H -0.1869 -0.1429 0.1201 0.067 Uiso 1 d
H21 H -0.2248 -0.1590 -0.0430 0.067 Uiso 1 d
H22 H -0.2775 0.1498 -0.0961 0.041 Uiso 1 d
H23 H -0.2451 0.1863 0.1551 0.061 Uiso 1 d
H24 H -0.3632 0.1499 0.2050 0.061 Uiso 1 d
H25 H -0.3623 0.2517 -0.0033 0.077 Uiso 1 d
H26 H -0.4107 0.2590 0.1589 0.077 Uiso 1 d
H27 H -0.5804 0.2467 -0.0077 0.078 Uiso 1 d
H28 H -0.5781 0.1887 0.1029 0.078 Uiso 1 d
H29 H -0.4837 0.1824 -0.1932 0.075 Uiso 1 d
H30 H -0.6020 0.1466 -0.1421 0.075 Uiso 1 d
H31 H -0.4831 0.0790 0.0136 0.056 Uiso 1 d
H32 H -0.4359 0.0727 -0.1493 0.056 Uiso 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C1 C3 123.3(14)
C8 C1 C2 119.7(12)
C3 C1 C2 58.9(10)
C6 C2 C3 123.5(16)
C6 C2 C1 122.5(12)
C3 C2 C1 60.0(10)
C5 C3 C2 119.8(12)
C5 C3 C4 114.6(16)
C2 C3 C4 116.6(17)
C5 C3 C1 120.1(13)
C2 C3 C1 61.2(10)
C4 C3 C1 114.2(14)
O7 C6 C2 122.6(18)
O9 C8 N10 120.6(11)
O9 C8 C1 123.4(11)
N10 C8 C1 116.0(12)
C8 N10 C11 122.3(10)
C8 N10 C20 118.8(10)
C11 N10 C20 118.2(9)
O12 C11 N13 125.0(12)
O12 C11 N10 120.0(13)
N13 C11 N10 114.9(15)
C11 N13 C14 123.3(12)
N13 C14 C19 112.1(10)
N13 C14 C15 108.9(12)
C19 C14 C15 111.2(13)
C14 C15 C16 109.7(15)
C17 C16 C15 111.8(19)
C16 C17 C18 109.8(15)
C17 C18 C19 110.0(15)
C14 C19 C18 110.7(12)
N10 C20 C25 111.0(10)
N10 C20 C21 111.7(12)
C25 C20 C21 111.5(11)
C22 C21 C20 109.5(12)
C21 C22 C23 112.2(12)
C24 C23 C22 109.9(13)
C23 C24 C25 111.8(14)
C20 C25 C24 108.8(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.48(2)
C1 C3 1.51(2)
C1 C2 1.53(2)
C2 C6 1.46(2)
C2 C3 1.50(2)
C3 C5 1.49(3)
C3 C4 1.51(2)
C6 O7 1.20(2)
C8 O9 1.226(15)
C8 N10 1.38(2)
N10 C11 1.42(2)
N10 C20 1.49(2)
C11 O12 1.24(2)
C11 N13 1.32(2)
N13 C14 1.46(2)
C14 C19 1.50(2)
C14 C15 1.52(2)
C15 C16 1.53(2)
C16 C17 1.49(3)
C17 C18 1.52(3)
C18 C19 1.53(2)
C20 C25 1.51(2)
C20 C21 1.52(2)
C21 C22 1.50(2)
C22 C23 1.53(2)
C23 C24 1.50(3)
C24 C25 1.53(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10871766
