#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/35/1513527.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_1513527
loop_
_publ_author_name
'Rana, Anup'
'Panda, Pradeepta K.'
_publ_section_title
;
 β-Octamethoxyporphycenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              78
_journal_page_last               81
_journal_paper_doi               10.1021/ol403068j
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C7 H8 N O3'
_chemical_formula_weight         154.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.220(14)
_cell_angle_beta                 82.897(15)
_cell_angle_gamma                85.329(14)
_cell_formula_units_Z            2
_cell_length_a                   4.379(4)
_cell_length_b                   8.588(8)
_cell_length_c                   9.945(9)
_cell_measurement_reflns_used    1074
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      0.926
_cell_volume                     361.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3963
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             162
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0859P)²+0.0899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                1141
_reflns_number_total             1666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403068j_si_007.cif
_cod_data_source_block           anup_s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        361.4(5)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1513527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O 1.0602(5) 0.2816(2) 0.3228(2) 0.0455(6) Uani 1 1 d .
N1 N 0.7662(5) -0.1034(3) 0.4085(2) 0.0359(6) Uani 1 1 d .
O1 O 0.4025(5) -0.2808(2) 0.2833(2) 0.0595(7) Uani 1 1 d .
C3 C 0.7502(6) 0.1030(3) 0.2305(3) 0.0387(7) Uani 1 1 d .
C1 C 0.9256(6) 0.0105(3) 0.4382(3) 0.0334(6) Uani 1 1 d .
C4 C 0.6557(6) -0.0506(3) 0.2825(3) 0.0376(7) Uani 1 1 d .
O2 O 0.6766(5) 0.1911(3) 0.1064(2) 0.0589(7) Uani 1 1 d .
C2 C 0.9170(6) 0.1428(3) 0.3285(3) 0.0371(7) Uani 1 1 d .
C5 C 0.4747(7) -0.1474(4) 0.2261(3) 0.0441(7) Uani 1 1 d .
C7 C 0.8509(9) 0.4126(3) 0.3445(4) 0.0643(10) Uani 1 1 d .
H7A H 0.6928 0.4250 0.2836 0.096 Uiso 1 1 calc R
H7B H 0.9606 0.5088 0.3255 0.096 Uiso 1 1 calc R
H7C H 0.7589 0.3920 0.4390 0.096 Uiso 1 1 calc R
C6 C 0.8945(11) 0.2891(6) 0.0247(4) 0.0953(17) Uani 1 1 d .
H6A H 0.9249 0.3746 0.0688 0.143 Uiso 1 1 calc R
H6B H 0.8242 0.3328 -0.0643 0.143 Uiso 1 1 calc R
H6C H 1.0857 0.2280 0.0130 0.143 Uiso 1 1 calc R
H1 H 0.729(7) -0.191(4) 0.464(3) 0.042(8) Uiso 1 1 d .
H2 H 0.401(7) -0.094(4) 0.138(4) 0.057(9) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0470(12) 0.0381(10) 0.0522(13) -0.0036(9) -0.0134(10) -0.0123(9)
N1 0.0377(13) 0.0329(12) 0.0368(13) -0.0049(10) -0.0052(10) -0.0054(10)
O1 0.0687(16) 0.0470(13) 0.0678(16) -0.0118(11) -0.0184(12) -0.0165(11)
C3 0.0366(16) 0.0461(15) 0.0333(15) -0.0058(12) -0.0075(12) -0.0024(12)
C1 0.0302(14) 0.0349(13) 0.0351(14) -0.0085(11) -0.0027(11) -0.0004(11)
C4 0.0359(16) 0.0428(15) 0.0353(15) -0.0090(12) -0.0072(12) -0.0021(12)
O2 0.0578(14) 0.0697(15) 0.0447(13) 0.0106(11) -0.0200(11) -0.0189(12)
C2 0.0335(15) 0.0389(14) 0.0379(15) -0.0053(12) -0.0044(12) -0.0030(11)
C5 0.0431(18) 0.0488(17) 0.0432(18) -0.0108(14) -0.0117(14) -0.0053(14)
C7 0.077(3) 0.0408(17) 0.079(3) -0.0214(17) -0.007(2) -0.0101(17)
C6 0.113(4) 0.117(4) 0.053(2) 0.020(2) -0.028(2) -0.068(3)
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_3
C2 O3 C7 113.6(2) .
C1 N1 C4 110.4(2) .
C1 N1 H1 123(2) .
C4 N1 H1 126(2) .
O2 C3 C4 122.3(2) .
O2 C3 C2 130.0(3) .
C4 C3 C2 107.6(2) .
N1 C1 C2 107.6(2) .
N1 C1 C1 123.5(3) 2_756
C2 C1 C1 128.9(3) 2_756
N1 C4 C3 107.2(2) .
N1 C4 C5 122.1(3) .
C3 C4 C5 130.7(3) .
C3 O2 C6 118.2(3) .
O3 C2 C1 123.6(2) .
O3 C2 C3 129.2(3) .
C1 C2 C3 107.2(2) .
O1 C5 C4 124.5(3) .
O1 C5 H2 121.2(18) .
C4 C5 H2 114.2(18) .
O3 C7 H7A 109.5 .
O3 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
O3 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
O2 C6 H6A 109.5 .
O2 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
O2 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C2 1.379(3) .
O3 C7 1.429(4) .
N1 C1 1.350(3) .
N1 C4 1.369(4) .
N1 H1 0.84(3) .
O1 C5 1.210(4) .
C3 O2 1.358(4) .
C3 C4 1.383(4) .
C3 C2 1.402(4) .
C1 C2 1.391(4) .
C1 C1 1.431(5) 2_756
C4 C5 1.434(4) .
O2 C6 1.384(4) .
C5 H2 0.98(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
