#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028798.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_4028798
loop_
_publ_author_name
'Ping Cheng'
'Wenjie Shao'
'Derrick L. J. Clive'
_publ_section_title
;
 A General Route to 1,3'-Bipyrroles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11860
_journal_page_last               11873
_journal_paper_doi               10.1021/jo401892t
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C15 H17 N O7'
_chemical_formula_sum            'C15 H17 N O7'
_chemical_formula_weight         323.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.0466(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0112(5)
_cell_length_b                   17.0294(9)
_cell_length_c                   10.0896(5)
_cell_measurement_reflns_used    6669
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      2.39
_cell_volume                     1615.91(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12867
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.5398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2748
_reflns_number_total             3317
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo401892t_si_001.cif
_cod_data_source_block           dlc1217
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028798
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26649(10) 0.13551(6) 0.34616(10) 0.0314(2) Uani 1 1 d . B .
O2 O 0.12064(12) 0.14864(7) 0.53347(10) 0.0445(3) Uani 1 1 d . . .
O3 O -0.06609(11) 0.08565(6) 0.38147(10) 0.0384(3) Uani 1 1 d . . .
O4 O -0.14035(11) 0.15788(6) -0.03757(10) 0.0378(3) Uani 1 1 d . . .
O5 O -0.06476(10) 0.19415(6) -0.21432(10) 0.0346(2) Uani 1 1 d . . .
O6 O 0.28067(11) -0.04025(6) 0.30122(10) 0.0361(2) Uani 1 1 d . . .
O7 O 0.46388(10) -0.02310(7) 0.22414(11) 0.0405(3) Uani 1 1 d . . .
N N 0.12410(11) 0.07109(6) 0.07963(11) 0.0260(2) Uani 1 1 d . . .
C1 C 0.07554(14) 0.10687(8) -0.05157(13) 0.0266(3) Uani 1 1 d . . .
C2 C 0.17022(15) 0.09120(8) -0.11973(14) 0.0305(3) Uani 1 1 d . . .
H2 H 0.1624 0.1082 -0.2118 0.037 Uiso 1 1 calc R . .
C3 C 0.27994(15) 0.04585(8) -0.02921(14) 0.0310(3) Uani 1 1 d . . .
H3 H 0.3602 0.0264 -0.0487 0.037 Uiso 1 1 calc R . .
C4 C 0.25120(14) 0.03440(8) 0.09327(14) 0.0277(3) Uani 1 1 d . . .
C5 C 0.06045(14) 0.07905(8) 0.18519(13) 0.0263(3) Uani 1 1 d . . .
H5 H -0.0341 0.0610 0.1657 0.032 Uiso 1 1 calc R . .
C6 C 0.12890(14) 0.11081(7) 0.30949(13) 0.0262(3) Uani 1 1 d . . .
C7 C 0.28176(18) 0.21960(10) 0.3426(2) 0.0515(4) Uani 1 1 d D . .
H7A H 0.2639 0.2439 0.4241 0.062 Uiso 0.85 1 calc PR A 1
H7B H 0.2123 0.2412 0.2549 0.062 Uiso 0.85 1 calc PR A 1
H7C H 0.2356 0.2435 0.4053 0.062 Uiso 0.15 1 calc PR A 2
H7D H 0.2300 0.2381 0.2455 0.062 Uiso 0.15 1 calc PR A 2
C8A C 0.4286(3) 0.2370(2) 0.3483(3) 0.0517(8) Uani 0.85 1 d P B 1
H8A H 0.4634 0.2094 0.2850 0.062 Uiso 0.85 1 calc PR B 1
C9A C 0.5135(2) 0.28722(13) 0.4338(3) 0.0598(6) Uani 0.85 1 d P B 1
H9A H 0.4825 0.3159 0.4986 0.072 Uiso 0.85 1 calc PR B 1
H9B H 0.6065 0.2952 0.4312 0.072 Uiso 0.85 1 calc PR B 1
C8B C 0.4312(12) 0.2487(15) 0.386(2) 0.052 Uiso 0.15 1 d PD B 2
H8B H 0.4568 0.3000 0.4231 0.062 Uiso 0.15 1 calc PR B 2
C9B C 0.5204(16) 0.2019(8) 0.3708(14) 0.060 Uiso 0.15 1 d P B 2
H9C H 0.4916 0.1510 0.3334 0.072 Uiso 0.15 1 calc PR B 2
H9D H 0.6173 0.2172 0.3965 0.072 Uiso 0.15 1 calc PR B 2
C10 C 0.06298(15) 0.11766(8) 0.42109(14) 0.0299(3) Uani 1 1 d . . .
C11 C -0.13780(19) 0.08961(11) 0.48365(18) 0.0494(4) Uani 1 1 d . . .
H11A H -0.2307 0.0639 0.4453 0.059 Uiso 1 1 calc R . .
H11B H -0.1510 0.1447 0.5044 0.059 Uiso 1 1 calc R . .
H11C H -0.0803 0.0630 0.5706 0.059 Uiso 1 1 calc R . .
C12 C -0.05427(14) 0.15431(8) -0.09695(13) 0.0282(3) Uani 1 1 d . . .
C13 C -0.19539(16) 0.23727(9) -0.27640(16) 0.0398(4) Uani 1 1 d . . .
H13A H -0.1924 0.2656 -0.3599 0.048 Uiso 1 1 calc R . .
H13B H -0.2068 0.2749 -0.2075 0.048 Uiso 1 1 calc R . .
H13C H -0.2758 0.2007 -0.3040 0.048 Uiso 1 1 calc R . .
C14 C 0.32936(14) -0.01304(8) 0.21772(14) 0.0292(3) Uani 1 1 d . . .
C15 C 0.55148(17) -0.06934(11) 0.34288(17) 0.0458(4) Uani 1 1 d . . .
H15A H 0.6476 -0.0738 0.3389 0.055 Uiso 1 1 calc R . .
H15B H 0.5101 -0.1218 0.3388 0.055 Uiso 1 1 calc R . .
H15C H 0.5558 -0.0436 0.4311 0.055 Uiso 1 1 calc R . .
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
C6 O1 C7 113.90(11)
C10 O3 C11 115.77(12)
C12 O5 C13 115.29(11)
C14 O7 C15 115.06(11)
C4 N C1 107.68(10)
C4 N C5 127.02(11)
C1 N C5 124.96(11)
C2 C1 N 108.45(11)
C2 C1 C12 129.88(12)
N C1 C12 121.65(11)
C1 C2 C3 107.63(12)
C4 C3 C2 107.83(12)
C3 C4 N 108.39(11)
C3 C4 C14 129.07(12)
N C4 C14 122.36(11)
C6 C5 N 122.00(12)
C5 C6 O1 122.04(12)
C5 C6 C10 121.92(12)
O1 C6 C10 115.96(11)
O1 C7 C8A 108.04(18)
O1 C7 C8B 115.3(10)
C9A C8A C7 124.8(2)
C9B C8B C7 116.2(17)
O2 C10 O3 124.41(13)
O2 C10 C6 123.49(13)
O3 C10 C6 112.10(11)
O4 C12 O5 124.12(13)
O4 C12 C1 125.47(12)
O5 C12 C1 110.41(11)
O6 C14 O7 124.09(13)
O6 C14 C4 125.79(12)
O7 C14 C4 110.11(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.3645(16)
O1 C7 1.4419(19)
O2 C10 1.2035(17)
O3 C10 1.3314(17)
O3 C11 1.4458(16)
O4 C12 1.2080(16)
O5 C12 1.3373(16)
O5 C13 1.4423(17)
O6 C14 1.2016(16)
O7 C14 1.3368(16)
O7 C15 1.4505(18)
N C4 1.3814(17)
N C1 1.3852(16)
N C5 1.4227(16)
C1 C2 1.3746(18)
C1 C12 1.4640(19)
C2 C3 1.3961(19)
C3 C4 1.3755(18)
C4 C14 1.4723(19)
C5 C6 1.3213(18)
C6 C10 1.4921(18)
C7 C8A 1.481(3)
C7 C8B 1.492(7)
C8A C9A 1.302(3)
C8B C9B 1.24(3)
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 N C1 C2 1.16(15)
C5 N C1 C2 174.88(12)
C4 N C1 C12 -177.04(12)
C5 N C1 C12 -3.33(19)
N C1 C2 C3 -0.67(15)
C12 C1 C2 C3 177.34(13)
C1 C2 C3 C4 -0.08(16)
C2 C3 C4 N 0.80(15)
C2 C3 C4 C14 176.05(13)
C1 N C4 C3 -1.21(15)
C5 N C4 C3 -174.76(12)
C1 N C4 C14 -176.84(12)
C5 N C4 C14 9.6(2)
C4 N C5 C6 54.96(19)
C1 N C5 C6 -117.53(15)
N C5 C6 O1 -2.29(19)
N C5 C6 C10 -178.77(11)
C7 O1 C6 C5 104.43(16)
C7 O1 C6 C10 -78.90(15)
C6 O1 C7 C8A -165.83(14)
C6 O1 C7 C8B 178.4(9)
O1 C7 C8A C9A -130.8(3)
O1 C7 C8B C9B 25(2)
C11 O3 C10 O2 -0.1(2)
C11 O3 C10 C6 179.93(12)
C5 C6 C10 O2 -177.40(13)
O1 C6 C10 O2 5.92(19)
C5 C6 C10 O3 2.59(18)
O1 C6 C10 O3 -174.09(11)
C13 O5 C12 O4 -5.93(19)
C13 O5 C12 C1 174.39(11)
C2 C1 C12 O4 171.01(14)
N C1 C12 O4 -11.2(2)
C2 C1 C12 O5 -9.3(2)
N C1 C12 O5 168.47(11)
C15 O7 C14 O6 -0.9(2)
C15 O7 C14 C4 -179.87(12)
C3 C4 C14 O6 -156.19(15)
N C4 C14 O6 18.5(2)
C3 C4 C14 O7 22.7(2)
N C4 C14 O7 -162.61(12)
