#------------------------------------------------------------------------------
#$Date: 2018-11-27 04:58:46 +0200 (Tue, 27 Nov 2018) $
#$Revision: 212196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/18/7231879.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_7231879
loop_
_publ_author_name
'Ono, Toshikazu'
'Xu, Ning'
'Koga, Daiki'
'Ideo, Toshihiro'
'Sugimoto, Manabu'
'Hisaeda, Yoshio'
_publ_section_title
;
 Gram-scale synthesis of porphycenes through acid-catalyzed oxidative
 macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
;
_journal_issue                   69
_journal_name_full               'RSC Advances'
_journal_page_first              39269
_journal_paper_doi               10.1039/C8RA09040H
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C52 H46 N4'
_chemical_formula_weight         726.93
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2018-09-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.303(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7406(11)
_cell_length_b                   15.369(2)
_cell_length_c                   16.406(2)
_cell_measurement_reflns_used    658
_cell_measurement_temperature    103.0(2)
_cell_measurement_theta_max      30.3624
_cell_measurement_theta_min      2.5544
_cell_volume                     2144.8(5)
_computing_cell_refinement       'APEX3 v2017.7-RC3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.7 RC2'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.0(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32049
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.467
_refine_ls_extinction_coef       0.044(4)
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4877
_refine_ls_number_restraints     168
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0907P)²+1.2790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                3778
_reflns_number_total             4877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ra09040h2.cif
_cod_data_source_block           h911
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7231879
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
N N001 0.39430(16) 0.40163(9) 0.44376(9) 0.0191(3) Uani d U . 1
N N002 0.35850(17) 0.51808(9) 0.57512(9) 0.0195(3) Uani d U . 1
C C003 0.2684(2) 0.39876(11) 0.47880(11) 0.0199(4) Uani d U . 1
C C004 0.36951(19) 0.34168(11) 0.38061(10) 0.0192(4) Uani d U . 1
C C005 0.3067(2) 0.56592(11) 0.63358(10) 0.0208(4) Uani d U . 1
C C006 0.5274(2) 0.67815(11) 0.67242(10) 0.0201(4) Uani d U . 1
C C007 0.5861(2) 0.75076(12) 0.73311(11) 0.0229(4) Uani d U . 1
C C008 0.6381(2) 0.73224(13) 0.81811(11) 0.0262(4) Uani d U . 1
H H008 0.632415 0.674253 0.837256 0.031 Uiso calc U R 1
C C009 0.2186(2) 0.30019(12) 0.37571(11) 0.0234(4) Uani d U . 1
H H009 0.171609 0.256704 0.336771 0.028 Uiso calc U R 1
C C00A 0.1571(2) 0.33500(12) 0.43699(12) 0.0242(4) Uani d U . 1
H H00A 0.059724 0.320248 0.449827 0.029 Uiso calc U R 1
C C00B 0.3833(2) 0.63932(11) 0.67723(10) 0.0210(4) Uani d U . 1
C C00C 0.2527(2) 0.45456(11) 0.54426(11) 0.0200(4) Uani d U . 1
C C00D 0.5934(2) 0.83594(12) 0.70583(12) 0.0264(4) Uani d U . 1
H H00D 0.557029 0.849015 0.648008 0.032 Uiso calc U R 1
C C00E 0.1274(2) 0.46027(12) 0.58640(11) 0.0247(4) Uani d U . 1
H H00E 0.038027 0.423289 0.578255 0.03 Uiso calc U R 1
C C00F 0.1597(2) 0.52872(12) 0.64060(11) 0.0248(4) Uani d U . 1
H H00F 0.095967 0.548326 0.676668 0.03 Uiso calc U R 1
C C00G 0.2897(2) 0.68269(13) 0.73218(12) 0.0285(4) Uani d U . 1
C C00H 0.6983(2) 0.79740(14) 0.87535(12) 0.0303(5) Uani d U . 1
C C00I 0.7056(2) 0.88172(14) 0.84621(13) 0.0323(5) Uani d U . 1
H H00I 0.747532 0.926433 0.884907 0.039 Uiso calc U R 1
C C00J 0.6531(2) 0.90257(13) 0.76187(14) 0.0313(5) Uani d U . 1
C C00K 0.2202(2) 0.76285(14) 0.70745(15) 0.0344(5) Uani d U . 1
H H00K 0.235368 0.789465 0.657646 0.041 Uiso calc U R 1
C C00L 0.2660(3) 0.64410(16) 0.80492(14) 0.0417(6) Uani d U . 1
H H00L 0.312727 0.589253 0.821915 0.05 Uiso calc U R 1
C C00M 0.7544(3) 0.77603(18) 0.96679(13) 0.0443(6) Uani d U . 1
H H00B 0.866932 0.78889 0.984956 0.066 Uiso calc U R 1
H H00C 0.736585 0.714139 0.975632 0.066 Uiso calc U R 1
H H00G 0.696247 0.811122 0.999385 0.066 Uiso calc U R 1
C C00N 0.6617(3) 0.99458(14) 0.73116(17) 0.0436(6) Uani d U . 1
H H00H 0.702095 1.032962 0.778967 0.065 Uiso calc U R 1
H H00J 0.556425 1.01389 0.702018 0.065 Uiso calc U R 1
H H00M 0.732072 0.996662 0.692546 0.065 Uiso calc U R 1
C C00O 0.1281(3) 0.80473(17) 0.75504(19) 0.0518(7) Uani d U . 1
C C00P 0.1749(4) 0.6845(2) 0.85333(18) 0.0598(8) Uani d U . 1
C C00Q 0.1077(3) 0.7644(2) 0.8272(2) 0.0642(9) Uani d U . 1
H H00Q 0.04566 0.79243 0.859971 0.077 Uiso calc U R 1
C C00R 0.0530(3) 0.89066(18) 0.7264(2) 0.0748(11) Uani d U . 1
H H00N -0.034845 0.881589 0.6779 0.112 Uiso calc U R 1
H H00O 0.130791 0.929154 0.710643 0.112 Uiso calc U R 1
H H00P 0.013891 0.917339 0.771937 0.112 Uiso calc U R 1
C C00S 0.1482(5) 0.6424(3) 0.9310(2) 0.0996(16) Uani d U . 1
H H00R 0.197172 0.677646 0.979853 0.149 Uiso calc U R 1
H H00S 0.195026 0.584134 0.936694 0.149 Uiso calc U R 1
H H00T 0.035057 0.637813 0.927453 0.149 Uiso calc U R 1
H H1N 0.450(4) 0.5371(18) 0.5537(18) 0.060(8) Uiso d . . 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C003 N001 C004 . . 107.30(14)
C00C N002 C005 . . 109.94(15)
C00C N002 H1N . . 128.0(16)
C005 N002 H1N . . 121.1(16)
N001 C003 C00C . . 122.43(15)
N001 C003 C00A . . 110.26(15)
C00C C003 C00A . . 127.26(16)
N001 C004 C006 . 3_666 126.61(15)
N001 C004 C009 . . 108.79(15)
C006 C004 C009 3_666 . 124.60(16)
N002 C005 C00B . . 126.03(16)
N002 C005 C00F . . 106.84(15)
C00B C005 C00F . . 127.13(16)
C00B C006 C004 . 3_666 129.96(16)
C00B C006 C007 . . 116.68(15)
C004 C006 C007 3_666 . 113.35(15)
C00D C007 C008 . . 119.11(17)
C00D C007 C006 . . 121.28(16)
C008 C007 C006 . . 119.59(16)
C00H C008 C007 . . 120.95(19)
C00H C008 H008 . . 119.5
C007 C008 H008 . . 119.5
C00A C009 C004 . . 107.23(15)
C00A C009 H009 . . 126.4
C004 C009 H009 . . 126.4
C009 C00A C003 . . 106.41(16)
C009 C00A H00A . . 126.8
C003 C00A H00A . . 126.8
C006 C00B C005 . . 129.14(16)
C006 C00B C00G . . 117.45(15)
C005 C00B C00G . . 113.32(15)
N002 C00C C003 . . 123.01(15)
N002 C00C C00E . . 107.93(15)
C003 C00C C00E . . 128.97(16)
C007 C00D C00J . . 121.14(19)
C007 C00D H00D . . 119.4
C00J C00D H00D . . 119.4
C00F C00E C00C . . 107.25(16)
C00F C00E H00E . . 126.4
C00C C00E H00E . . 126.4
C00E C00F C005 . . 108.04(16)
C00E C00F H00F . . 126.0
C005 C00F H00F . . 126.0
C00L C00G C00K . . 119.1(2)
C00L C00G C00B . . 122.3(2)
C00K C00G C00B . . 118.57(18)
C00I C00H C008 . . 118.68(19)
C00I C00H C00M . . 121.17(19)
C008 C00H C00M . . 120.2(2)
C00H C00I C00J . . 121.79(18)
C00H C00I H00I . . 119.1
C00J C00I H00I . . 119.1
C00I C00J C00D . . 118.31(19)
C00I C00J C00N . . 121.16(19)
C00D C00J C00N . . 120.5(2)
C00G C00K C00O . . 120.8(2)
C00G C00K H00K . . 119.6
C00O C00K H00K . . 119.6
C00G C00L C00P . . 121.1(3)
C00G C00L H00L . . 119.5
C00P C00L H00L . . 119.5
C00H C00M H00B . . 109.5
C00H C00M H00C . . 109.5
H00B C00M H00C . . 109.5
C00H C00M H00G . . 109.5
H00B C00M H00G . . 109.5
H00C C00M H00G . . 109.5
C00J C00N H00H . . 109.5
C00J C00N H00J . . 109.5
H00H C00N H00J . . 109.5
C00J C00N H00M . . 109.5
H00H C00N H00M . . 109.5
H00J C00N H00M . . 109.5
C00Q C00O C00K . . 118.3(3)
C00Q C00O C00R . . 121.9(2)
C00K C00O C00R . . 119.7(3)
C00Q C00P C00L . . 118.4(3)
C00Q C00P C00S . . 120.6(3)
C00L C00P C00S . . 121.0(3)
C00O C00Q C00P . . 122.2(2)
C00O C00Q H00Q . . 118.9
C00P C00Q H00Q . . 118.9
C00O C00R H00N . . 109.5
C00O C00R H00O . . 109.5
H00N C00R H00O . . 109.5
C00O C00R H00P . . 109.5
H00N C00R H00P . . 109.5
H00O C00R H00P . . 109.5
C00P C00S H00R . . 109.5
C00P C00S H00S . . 109.5
H00R C00S H00S . . 109.5
C00P C00S H00T . . 109.5
H00R C00S H00T . . 109.5
H00S C00S H00T . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N001 C003 . 1.354(2)
N001 C004 . 1.366(2)
N002 C00C . 1.360(2)
N002 C005 . 1.366(2)
N002 H1N . 0.99(3)
C003 C00C . 1.406(2)
C003 C00A . 1.439(2)
C004 C006 3_666 1.422(2)
C004 C009 . 1.451(2)
C005 C00B . 1.419(2)
C005 C00F . 1.435(2)
C006 C00B . 1.412(2)
C006 C007 . 1.505(2)
C007 C00D . 1.390(3)
C007 C008 . 1.393(3)
C008 C00H . 1.391(3)
C008 H008 . 0.95
C009 C00A . 1.354(3)
C009 H009 . 0.95
C00A H00A . 0.95
C00B C00G . 1.505(2)
C00C C00E . 1.426(2)
C00D C00J . 1.395(3)
C00D H00D . 0.95
C00E C00F . 1.364(3)
C00E H00E . 0.95
C00F H00F . 0.95
C00G C00L . 1.390(3)
C00G C00K . 1.392(3)
C00H C00I . 1.388(3)
C00H C00M . 1.503(3)
C00I C00J . 1.391(3)
C00I H00I . 0.95
C00J C00N . 1.509(3)
C00K C00O . 1.400(3)
C00K H00K . 0.95
C00L C00P . 1.394(3)
C00L H00L . 0.95
C00M H00B . 0.98
C00M H00C . 0.98
C00M H00G . 0.98
C00N H00H . 0.98
C00N H00J . 0.98
C00N H00M . 0.98
C00O C00Q . 1.384(4)
C00O C00R . 1.501(4)
C00P C00Q . 1.385(5)
C00P C00S . 1.495(4)
C00Q H00Q . 0.95
C00R H00N . 0.98
C00R H00O . 0.98
C00R H00P . 0.98
C00S H00R . 0.98
C00S H00S . 0.98
C00S H00T . 0.98
