#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:11:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180292 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150618.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_7150618
loop_
_publ_author_name
'Reyes-Gutiérrez, Paul E.'
'Torres-Ochoa, Rubén O.'
'Martínez, Roberto'
'Miranda, Luis D.'
_publ_section_title
;
 Synthesis of azepino[4,5-b]indolones via an intermolecular radical
 oxidative substitution of N-Boc tryptamine
;
_journal_issue                   7
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1388
_journal_page_last               1396
_journal_paper_doi               10.1039/b821260k
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C15 H16 N2 O4'
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30
_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                93.177(2)
_cell_angle_beta                 97.768(2)
_cell_angle_gamma                109.836(2)
_cell_formula_units_Z            4
_cell_length_a                   10.7390(14)
_cell_length_b                   11.1934(15)
_cell_length_c                   12.1609(16)
_cell_measurement_reflns_used    5634
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.27
_cell_volume                     1354.4(3)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 7.34A (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 0.661
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14856
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         4968
_refine_ls_number_restraints     139
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0511
_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)+(0.0600P)²+0.6564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                3863
_reflns_number_total             4968
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821260k.txt
_cod_data_source_block           038MAR08
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               7150618
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59628(15) 0.62968(15) -0.06594(13) 0.0291(4) Uani 1 1 d . . .
O2 O 0.80344(16) 0.82751(16) -0.06993(13) 0.0284(4) Uani 1 1 d D . .
H2 H 0.721(2) 0.794(3) -0.102(2) 0.043 Uiso 1 1 d D . .
O3 O 0.87675(18) 0.97635(16) 0.13477(15) 0.0389(5) Uani 1 1 d . A .
C1 C 0.8940(2) 0.5485(2) 0.15997(18) 0.0250(5) Uani 1 1 d . . .
H1A H 0.9500 0.5402 0.2288 0.030 Uiso 1 1 calc R . .
H1B H 0.8656 0.4671 0.1109 0.030 Uiso 1 1 calc R . .
C2 C 0.7707(2) 0.5708(2) 0.19033(18) 0.0235(5) Uani 1 1 d . . .
H2A H 0.7283 0.5062 0.2392 0.028 Uiso 1 1 calc R . .
H2B H 0.7983 0.6561 0.2329 0.028 Uiso 1 1 calc R . .
N3 N 0.67237(18) 0.56322(18) 0.09199(15) 0.0239(4) Uani 1 1 d D . .
H3 H 0.599(2) 0.502(2) 0.080(2) 0.029 Uiso 1 1 d D . .
C3 C 0.6830(2) 0.6451(2) 0.01706(18) 0.0226(5) Uani 1 1 d . . .
C5 C 0.8078(2) 0.7690(2) 0.03052(17) 0.0224(5) Uani 1 1 d . A .
N6 N 1.04698(19) 0.83082(19) 0.01359(16) 0.0265(4) Uani 1 1 d D . .
H6 H 1.046(3) 0.893(2) -0.022(2) 0.032 Uiso 1 1 d D . .
C7 C 1.2844(2) 0.8440(3) 0.0099(2) 0.0340(6) Uani 1 1 d . . .
H7 H 1.3101 0.9184 -0.0279 0.041 Uiso 1 1 calc R . .
C8 C 1.3732(2) 0.7826(3) 0.0416(2) 0.0386(6) Uani 1 1 d . . .
H8 H 1.4616 0.8153 0.0248 0.046 Uiso 1 1 calc R . .
C9 C 1.3360(2) 0.6734(3) 0.0979(2) 0.0354(6) Uani 1 1 d . . .
H9 H 1.3998 0.6339 0.1191 0.043 Uiso 1 1 calc R . .
C10 C 1.2079(2) 0.6220(2) 0.12323(19) 0.0310(6) Uani 1 1 d . . .
H10 H 1.1832 0.5479 0.1616 0.037 Uiso 1 1 calc R . .
C11 C 1.1150(2) 0.6821(2) 0.09081(18) 0.0263(5) Uani 1 1 d . . .
C12 C 0.9765(2) 0.6543(2) 0.10174(18) 0.0235(5) Uani 1 1 d . . .
C13 C 0.9391(2) 0.7468(2) 0.05193(18) 0.0234(5) Uani 1 1 d . . .
C14 C 1.1553(2) 0.7923(2) 0.03570(19) 0.0286(5) Uani 1 1 d . . .
C15 C 0.8002(2) 0.8678(2) 0.12010(18) 0.0235(5) Uani 1 1 d . . .
O4 O 0.6967(2) 0.82314(18) 0.17226(19) 0.0323(5) Uani 0.925(4) 1 d PDU A 1
C16 C 0.6792(3) 0.9115(3) 0.2580(2) 0.0331(7) Uani 0.925(4) 1 d PDU A 1
H16A H 0.6989 0.9968 0.2311 0.040 Uiso 0.925(4) 1 calc PR A 1
H16B H 0.5845 0.8806 0.2698 0.040 Uiso 0.925(4) 1 calc PR A 1
C17 C 0.7665(5) 0.9231(5) 0.3642(3) 0.0717(13) Uani 0.925(4) 1 d PDU A 1
H17A H 0.7500 0.9811 0.4191 0.108 Uiso 0.925(4) 1 calc PR A 1
H17B H 0.8605 0.9572 0.3537 0.108 Uiso 0.925(4) 1 calc PR A 1
H17C H 0.7475 0.8389 0.3912 0.108 Uiso 0.925(4) 1 calc PR A 1
O4B O 0.752(3) 0.828(3) 0.215(2) 0.040(3) Uani 0.075(4) 1 d PDU A 2
C16B C 0.716(4) 0.843(3) 0.333(2) 0.043(3) Uani 0.075(4) 1 d PDU A 2
H16C H 0.6297 0.8573 0.3305 0.052 Uiso 0.075(4) 1 calc PR A 2
H16D H 0.7143 0.7691 0.3748 0.052 Uiso 0.075(4) 1 calc PR A 2
C17B C 0.833(5) 0.959(5) 0.378(4) 0.060(6) Uani 0.075(4) 1 d PDU A 2
H17D H 0.9077 0.9348 0.4116 0.090 Uiso 0.075(4) 1 calc PR A 2
H17E H 0.8085 1.0089 0.4350 0.090 Uiso 0.075(4) 1 calc PR A 2
H17F H 0.8602 1.0116 0.3174 0.090 Uiso 0.075(4) 1 calc PR A 2
O21 O 0.50270(14) 0.56678(14) 0.64164(12) 0.0244(4) Uani 1 1 d . . .
O22 O 0.45214(16) 0.72664(15) 0.77400(12) 0.0260(4) Uani 1 1 d D . .
H22 H 0.495(3) 0.675(2) 0.778(2) 0.039 Uiso 1 1 d D . .
O23 O 0.46858(17) 0.96049(15) 0.62148(13) 0.0308(4) Uani 1 1 d . A .
C21 C 0.2203(2) 0.6668(2) 0.41755(18) 0.0231(5) Uani 1 1 d . . .
H21A H 0.1802 0.7141 0.3658 0.028 Uiso 1 1 calc R . .
H21B H 0.1775 0.5746 0.3912 0.028 Uiso 1 1 calc R . .
C22 C 0.3700(2) 0.7076(2) 0.41333(18) 0.0235(5) Uani 1 1 d . . .
H22A H 0.3829 0.6972 0.3348 0.028 Uiso 1 1 calc R . .
H22B H 0.4134 0.7993 0.4414 0.028 Uiso 1 1 calc R . .
N23 N 0.43548(18) 0.63369(18) 0.47967(16) 0.0229(4) Uani 1 1 d D . .
H23 H 0.452(2) 0.576(2) 0.4430(19) 0.027 Uiso 1 1 d D . .
C24 C 0.4572(2) 0.6387(2) 0.58989(18) 0.0205(5) Uani 1 1 d . . .
C25 C 0.4220(2) 0.7393(2) 0.65956(18) 0.0214(5) Uani 1 1 d . A .
N26 N 0.20647(18) 0.73262(18) 0.71697(15) 0.0222(4) Uani 1 1 d D . .
H26 H 0.245(2) 0.747(2) 0.7848(15) 0.027 Uiso 1 1 d D . .
C27 C -0.0326(2) 0.7108(2) 0.7264(2) 0.0256(5) Uani 1 1 d . . .
H27 H -0.0221 0.7272 0.8052 0.031 Uiso 1 1 calc R . .
C28 C -0.1541(2) 0.6869(2) 0.6595(2) 0.0280(5) Uani 1 1 d . . .
H28 H -0.2290 0.6872 0.6930 0.034 Uiso 1 1 calc R . .
C29 C -0.1706(2) 0.6619(2) 0.5432(2) 0.0272(5) Uani 1 1 d . . .
H29 H -0.2559 0.6463 0.4995 0.033 Uiso 1 1 calc R . .
C30 C -0.0647(2) 0.6598(2) 0.4913(2) 0.0256(5) Uani 1 1 d . . .
H30 H -0.0765 0.6424 0.4125 0.031 Uiso 1 1 calc R . .
C31 C 0.0608(2) 0.68370(19) 0.55724(18) 0.0208(5) Uani 1 1 d . . .
C32 C 0.1899(2) 0.68990(19) 0.53185(17) 0.0201(5) Uani 1 1 d . . .
C33 C 0.2748(2) 0.71885(19) 0.63131(17) 0.0192(5) Uani 1 1 d . . .
C34 C 0.0747(2) 0.7099(2) 0.67335(18) 0.0218(5) Uani 1 1 d . . .
C35 C 0.5100(2) 0.8771(2) 0.64419(18) 0.0236(5) Uani 1 1 d . . .
O24 O 0.6382(2) 0.8918(2) 0.6658(2) 0.0327(6) Uani 0.925(4) 1 d PDU A 1
C36 C 0.7320(3) 1.0236(3) 0.6648(4) 0.0376(8) Uani 0.925(4) 1 d PDU A 1
H36A H 0.7161 1.0540 0.5910 0.045 Uiso 0.925(4) 1 calc PR A 1
H36B H 0.7187 1.0820 0.7226 0.045 Uiso 0.925(4) 1 calc PR A 1
C37 C 0.8671(3) 1.0210(3) 0.6873(3) 0.0453(8) Uani 0.925(4) 1 d PDU A 1
H37A H 0.9320 1.1073 0.6875 0.068 Uiso 0.925(4) 1 calc PR A 1
H37B H 0.8792 0.9634 0.6293 0.068 Uiso 0.925(4) 1 calc PR A 1
H37C H 0.8815 0.9906 0.7603 0.068 Uiso 0.925(4) 1 calc PR A 1
O24B O 0.632(3) 0.856(3) 0.628(3) 0.035(5) Uani 0.075(4) 1 d PDU A 2
C36B C 0.706(5) 0.995(4) 0.658(6) 0.036(4) Uani 0.075(4) 1 d PDU A 2
H36C H 0.6524 1.0463 0.6298 0.043 Uiso 0.075(4) 1 calc PR A 2
H36D H 0.7337 1.0158 0.7400 0.043 Uiso 0.075(4) 1 calc PR A 2
C37B C 0.820(3) 1.013(3) 0.602(4) 0.046(6) Uani 0.075(4) 1 d PDU A 2
H37D H 0.8974 1.0842 0.6431 0.069 Uiso 0.075(4) 1 calc PR A 2
H37E H 0.7991 1.0331 0.5260 0.069 Uiso 0.075(4) 1 calc PR A 2
H37F H 0.8423 0.9351 0.5997 0.069 Uiso 0.075(4) 1 calc PR A 2
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 112.45(18) . . ?
N3 C2 C1 112.37(18) . . ?
C3 N3 C2 127.34(19) . . ?
O1 C3 N3 123.3(2) . . ?
O1 C3 C5 116.39(19) . . ?
N3 C3 C5 120.31(19) . . ?
O2 C5 C13 107.86(17) . . ?
O2 C5 C15 104.26(17) . . ?
C13 C5 C15 111.45(18) . . ?
O2 C5 C3 108.02(17) . . ?
C13 C5 C3 113.81(18) . . ?
C15 C5 C3 110.88(18) . . ?
C14 N6 C13 109.22(19) . . ?
C8 C7 C14 117.3(2) . . ?
C7 C8 C9 121.6(2) . . ?
C10 C9 C8 121.1(2) . . ?
C9 C10 C11 118.4(2) . . ?
C14 C11 C10 119.3(2) . . ?
C14 C11 C12 107.6(2) . . ?
C10 C11 C12 133.0(2) . . ?
C13 C12 C11 105.9(2) . . ?
C13 C12 C1 128.0(2) . . ?
C11 C12 C1 126.1(2) . . ?
C12 C13 N6 109.7(2) . . ?
C12 C13 C5 132.8(2) . . ?
N6 C13 C5 117.45(19) . . ?
N6 C14 C7 130.3(2) . . ?
N6 C14 C11 107.5(2) . . ?
C7 C14 C11 122.2(2) . . ?
O3 C15 O4 124.3(2) . . ?
O3 C15 O4B 111.9(12) . . ?
O3 C15 C5 122.5(2) . . ?
O4 C15 C5 113.06(19) . . ?
O4B C15 C5 119.5(12) . . ?
C15 O4 C16 117.2(2) . . ?
C17 C16 O4 112.3(3) . . ?
C15 O4B C16B 156(2) . . ?
C17B C16B O4B 97(2) . . ?
C32 C21 C22 113.40(18) . . ?
N23 C22 C21 112.66(18) . . ?
C24 N23 C22 126.63(19) . . ?
O21 C24 N23 124.1(2) . . ?
O21 C24 C25 117.20(19) . . ?
N23 C24 C25 118.67(18) . . ?
O22 C25 C33 108.70(17) . . ?
O22 C25 C35 105.58(17) . . ?
C33 C25 C35 111.46(17) . . ?
O22 C25 C24 108.88(17) . . ?
C33 C25 C24 110.54(17) . . ?
C35 C25 C24 111.50(17) . . ?
C34 N26 C33 109.12(18) . . ?
C28 C27 C34 117.1(2) . . ?
C27 C28 C29 121.8(2) . . ?
C30 C29 C28 121.0(2) . . ?
C29 C30 C31 118.7(2) . . ?
C34 C31 C30 119.1(2) . . ?
C34 C31 C32 107.54(18) . . ?
C30 C31 C32 133.4(2) . . ?
C33 C32 C31 106.29(18) . . ?
C33 C32 C21 128.2(2) . . ?
C31 C32 C21 125.47(19) . . ?
C32 C33 N26 109.77(19) . . ?
C32 C33 C25 131.6(2) . . ?
N26 C33 C25 118.58(18) . . ?
N26 C34 C27 130.3(2) . . ?
N26 C34 C31 107.26(19) . . ?
C27 C34 C31 122.4(2) . . ?
O23 C35 O24 124.4(2) . . ?
O23 C35 O24B 131.9(13) . . ?
O23 C35 C25 125.0(2) . . ?
O24 C35 C25 110.51(19) . . ?
O24B C35 C25 99.9(12) . . ?
C35 O24 C36 115.1(3) . . ?
C37 C36 O24 107.4(3) . . ?
C35 O24B C36B 89(2) . . ?
C37B C36B O24B 101(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.239(3) . ?
O2 C5 1.420(3) . ?
O3 C15 1.201(3) . ?
C1 C12 1.497(3) . ?
C1 C2 1.517(3) . ?
C2 N3 1.463(3) . ?
N3 C3 1.316(3) . ?
C3 C5 1.549(3) . ?
C5 C13 1.504(3) . ?
C5 C15 1.539(3) . ?
N6 C14 1.371(3) . ?
N6 C13 1.378(3) . ?
C7 C8 1.379(4) . ?
C7 C14 1.396(3) . ?
C8 C9 1.399(4) . ?
C9 C10 1.385(3) . ?
C10 C11 1.408(3) . ?
C11 C14 1.402(3) . ?
C11 C12 1.439(3) . ?
C12 C13 1.374(3) . ?
C15 O4 1.318(3) . ?
C15 O4B 1.36(3) . ?
O4 C16 1.472(3) . ?
C16 C17 1.461(5) . ?
O4B C16B 1.55(2) . ?
C16B C17B 1.49(2) . ?
O21 C24 1.234(2) . ?
O22 C25 1.412(3) . ?
O23 C35 1.193(3) . ?
C21 C32 1.499(3) . ?
C21 C22 1.524(3) . ?
C22 N23 1.465(3) . ?
N23 C24 1.324(3) . ?
C24 C25 1.549(3) . ?
C25 C33 1.506(3) . ?
C25 C35 1.548(3) . ?
N26 C34 1.373(3) . ?
N26 C33 1.383(3) . ?
C27 C28 1.374(3) . ?
C27 C34 1.398(3) . ?
C28 C29 1.401(3) . ?
C29 C30 1.380(3) . ?
C30 C31 1.404(3) . ?
C31 C34 1.403(3) . ?
C31 C32 1.440(3) . ?
C32 C33 1.362(3) . ?
C35 O24 1.317(3) . ?
C35 O24B 1.45(4) . ?
O24 C36 1.479(3) . ?
C36 C37 1.451(5) . ?
O24B C36B 1.48(2) . ?
C36B C37B 1.44(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.86(2) 1.99(3) 2.560(2) 123(2) .
N3 H3 O1 0.839(17) 2.090(18) 2.922(2) 171(2) 2_665
N6 H6 O3 0.847(17) 2.09(2) 2.866(3) 151(2) 2_775
O22 H22 O21 0.85(2) 2.03(3) 2.582(2) 122(2) .
O22 H22 O1 0.85(2) 2.23(3) 2.815(2) 126(2) 1_556
N23 H23 O21 0.843(17) 2.083(18) 2.926(2) 178(2) 2_666
