#------------------------------------------------------------------------------
#$Date: 2020-04-01 02:24:13 +0300 (Wed, 01 Apr 2020) $
#$Revision: 249881 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557692.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_1557692
loop_
_publ_author_name
'Kochanowska-Karamyan, Anna J.'
'Araujo, Hugo C.'
'Zhang, Xiong'
'El-Alfy, Abir'
'Carvalho, Paulo'
'Avery, Mitchell A.'
'Holmbo, Stephen D.'
'Magolan, Jakob'
'Hamann, Mark T.'
_publ_section_title
;
 Isolation and Synthesis of Veranamine, an Antidepressant Lead from the
 Marine Sponge Verongula rigida
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01107
_journal_year                    2020
_chemical_formula_moiety         'C15 H16 Br N2'
_chemical_formula_sum            'C15 H16 Br N2'
_chemical_formula_weight         304.21
_chemical_name_common            Veranamine
_chemical_name_systematic
8-bromo-4,5,5-trimethyl-5,6-dihydrobenzo[c][2,7]naphthyridine
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-05 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 107.0600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7086(2)
_cell_length_b                   9.7764(2)
_cell_length_c                   13.0365(3)
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.85
_cell_measurement_theta_min      4.72
_cell_volume                     1304.76(5)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5376
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.360
_diffrn_reflns_theta_min         4.717
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       Plates
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.087
_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     166
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0616P)²+1.6484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b01107_si_002.cif
_cod_data_source_block           Anna_2_0ma
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1557692
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.449
_shelx_estimated_absorpt_t_max   0.682
_publcif_funding_html
;
;
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.90686(3) -0.07483(4) 0.86193(3) 0.03149(16) Uani 1 1 d . . . . .
N1 N 0.4964(3) 0.0927(3) 0.1707(2) 0.0248(6) Uani 1 1 d . . . . .
N2 N 0.7938(2) 0.2211(3) 0.51192(19) 0.0211(5) Uani 1 1 d . . . . .
H10 H 0.8713 0.2552 0.5480 0.025 Uiso 1 1 calc R U . . .
H11 H 0.7338 0.2768 0.5238 0.025 Uiso 1 1 calc R U . . .
C1 C 0.6480(3) 0.2624(4) 0.1522(3) 0.0305(7) Uani 1 1 d . . . . .
H13 H 0.6214 0.2287 0.0798 0.046 Uiso 1 1 calc R U . . .
H1 H 0.7414 0.2701 0.1766 0.046 Uiso 1 1 calc R U . . .
H12 H 0.6096 0.3507 0.1545 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6032(3) 0.1646(3) 0.2238(2) 0.0230(6) Uani 1 1 d . . . . .
C3 C 0.6680(3) 0.1440(3) 0.3336(2) 0.0199(6) Uani 1 1 d . . . . .
C4 C 0.6283(3) 0.0321(3) 0.3851(3) 0.0201(6) Uani 1 1 d . . . . .
C5 C 0.7004(3) -0.0020(3) 0.4967(2) 0.0205(6) Uani 1 1 d . . . . .
C6 C 0.6880(3) -0.1279(3) 0.5453(3) 0.0243(7) Uani 1 1 d . . . . .
H15 H 0.6366 -0.1965 0.5043 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7503(3) -0.1519(3) 0.6527(3) 0.0271(7) Uani 1 1 d . . . . .
H16 H 0.7422 -0.2356 0.6840 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8251(3) -0.0480(3) 0.7124(2) 0.0243(7) Uani 1 1 d . . . . .
C9 C 0.5193(3) -0.0432(3) 0.3267(3) 0.0234(7) Uani 1 1 d . . . . .
H14 H 0.4903 -0.1173 0.3582 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4558(3) -0.0071(3) 0.2234(3) 0.0254(7) Uani 1 1 d . . . . .
H2 H 0.3803 -0.0545 0.1877 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7836(3) 0.2320(3) 0.3967(2) 0.0194(6) Uani 1 1 d . . . . .
C12 C 0.9103(3) 0.1794(4) 0.3767(2) 0.0242(7) Uani 1 1 d . . . . .
H3 H 0.9810 0.2403 0.4099 0.036 Uiso 1 1 calc R U . . .
H5 H 0.8989 0.1756 0.3009 0.036 Uiso 1 1 calc R U . . .
H4 H 0.9300 0.0896 0.4069 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7656(3) 0.3857(3) 0.3740(3) 0.0269(7) Uani 1 1 d . . . . .
H6 H 0.6791 0.4123 0.3735 0.040 Uiso 1 1 calc R U . . .
H7 H 0.7778 0.4054 0.3054 0.040 Uiso 1 1 calc R U . . .
H8 H 0.8286 0.4356 0.4288 0.040 Uiso 1 1 calc R U . . .
C14 C 0.7815(3) 0.0987(3) 0.5584(2) 0.0196(6) Uani 1 1 d . . . . .
C15 C 0.8427(3) 0.0766(3) 0.6682(3) 0.0226(6) Uani 1 1 d . . . . .
H9 H 0.8941 0.1444 0.7103 0.027 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C10 N1 C2 118.1(3) . . ?
C14 N2 C11 121.8(3) . . ?
C14 N2 H10 106.9 . . ?
C11 N2 H10 106.9 . . ?
C14 N2 H11 106.9 . . ?
C11 N2 H11 106.9 . . ?
H10 N2 H11 106.7 . . ?
C2 C1 H13 109.5 . . ?
C2 C1 H1 109.5 . . ?
H13 C1 H1 109.5 . . ?
C2 C1 H12 109.5 . . ?
H13 C1 H12 109.5 . . ?
H1 C1 H12 109.5 . . ?
N1 C2 C3 122.6(3) . . ?
N1 C2 C1 112.8(3) . . ?
C3 C2 C1 124.5(3) . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 C11 122.9(3) . . ?
C4 C3 C11 119.2(3) . . ?
C9 C4 C3 117.9(3) . . ?
C9 C4 C5 122.0(3) . . ?
C3 C4 C5 120.1(3) . . ?
C14 C5 C6 118.7(3) . . ?
C14 C5 C4 117.8(3) . . ?
C6 C5 C4 123.5(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H15 119.3 . . ?
C5 C6 H15 119.3 . . ?
C8 C7 C6 118.2(3) . . ?
C8 C7 H16 120.9 . . ?
C6 C7 H16 120.9 . . ?
C7 C8 C15 122.7(3) . . ?
C7 C8 Br1 119.4(2) . . ?
C15 C8 Br1 118.0(3) . . ?
C10 C9 C4 119.6(3) . . ?
C10 C9 H14 120.2 . . ?
C4 C9 H14 120.2 . . ?
N1 C10 C9 123.6(3) . . ?
N1 C10 H2 118.2 . . ?
C9 C10 H2 118.2 . . ?
N2 C11 C13 103.6(2) . . ?
N2 C11 C3 108.2(2) . . ?
C13 C11 C3 114.3(2) . . ?
N2 C11 C12 109.9(2) . . ?
C13 C11 C12 111.2(2) . . ?
C3 C11 C12 109.5(2) . . ?
C11 C12 H3 109.5 . . ?
C11 C12 H5 109.5 . . ?
H3 C12 H5 109.5 . . ?
C11 C12 H4 109.5 . . ?
H3 C12 H4 109.5 . . ?
H5 C12 H4 109.5 . . ?
C11 C13 H6 109.5 . . ?
C11 C13 H7 109.5 . . ?
H6 C13 H7 109.5 . . ?
C11 C13 H8 109.5 . . ?
H6 C13 H8 109.5 . . ?
H7 C13 H8 109.5 . . ?
N2 C14 C5 119.1(3) . . ?
N2 C14 C15 120.6(3) . . ?
C5 C14 C15 120.2(3) . . ?
C8 C15 C14 118.6(3) . . ?
C8 C15 H9 120.7 . . ?
C14 C15 H9 120.7 . . ?
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
Br1 C8 1.907(3) . ?
N1 C10 1.337(4) . ?
N1 C2 1.347(4) . ?
N2 C14 1.366(4) . ?
N2 C11 1.478(4) . ?
N2 H10 0.8900 . ?
N2 H11 0.8900 . ?
C1 C2 1.510(4) . ?
C1 H13 0.9600 . ?
C1 H1 0.9600 . ?
C1 H12 0.9600 . ?
C2 C3 1.410(4) . ?
C3 C4 1.412(4) . ?
C3 C11 1.534(4) . ?
C4 C9 1.401(5) . ?
C4 C5 1.472(4) . ?
C5 C14 1.400(5) . ?
C5 C6 1.409(4) . ?
C6 C7 1.383(5) . ?
C6 H15 0.9300 . ?
C7 C8 1.383(5) . ?
C7 H16 0.9300 . ?
C8 C15 1.384(4) . ?
C9 C10 1.366(5) . ?
C9 H14 0.9300 . ?
C10 H2 0.9300 . ?
C11 C13 1.532(4) . ?
C11 C12 1.543(4) . ?
C12 H3 0.9600 . ?
C12 H5 0.9600 . ?
C12 H4 0.9600 . ?
C13 H6 0.9600 . ?
C13 H7 0.9600 . ?
C13 H8 0.9600 . ?
C14 C15 1.405(5) . ?
C15 H9 0.9300 . ?
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
N2 H11 Br1 0.89 2.81 3.657(2) 159.1 2_656
N2 H10 N1 0.89 2.30 3.109(4) 150.6 4_666
N2 H11 Br1 0.89 2.81 3.657(2) 159.1 2_656
N2 H10 N1 0.89 2.30 3.109(4) 150.6 4_666
N2 H10 N1 0.89 2.30 3.109(4) 150.6 4_666
N2 H11 Br1 0.89 2.81 3.657(2) 159.1 2_656
N2 H10 N1 0.89 2.30 3.109(4) 150.6 4_666
N2 H11 Br1 0.89 2.81 3.657(2) 159.1 2_656
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C3 -4.0(4) . . . . ?
C10 N1 C2 C1 173.2(3) . . . . ?
N1 C2 C3 C4 8.1(4) . . . . ?
C1 C2 C3 C4 -168.7(3) . . . . ?
N1 C2 C3 C11 -175.5(3) . . . . ?
C1 C2 C3 C11 7.6(5) . . . . ?
C2 C3 C4 C9 -5.9(4) . . . . ?
C11 C3 C4 C9 177.6(2) . . . . ?
C2 C3 C4 C5 174.3(3) . . . . ?
C11 C3 C4 C5 -2.2(4) . . . . ?
C9 C4 C5 C14 -161.6(3) . . . . ?
C3 C4 C5 C14 18.2(4) . . . . ?
C9 C4 C5 C6 15.7(4) . . . . ?
C3 C4 C5 C6 -164.5(3) . . . . ?
C14 C5 C6 C7 2.1(4) . . . . ?
C4 C5 C6 C7 -175.2(3) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C15 -1.9(5) . . . . ?
C6 C7 C8 Br1 177.6(2) . . . . ?
C3 C4 C9 C10 0.2(4) . . . . ?
C5 C4 C9 C10 180.0(3) . . . . ?
C2 N1 C10 C9 -2.3(5) . . . . ?
C4 C9 C10 N1 4.2(5) . . . . ?
C14 N2 C11 C13 165.1(3) . . . . ?
C14 N2 C11 C3 43.4(3) . . . . ?
C14 N2 C11 C12 -76.1(3) . . . . ?
C2 C3 C11 N2 158.2(3) . . . . ?
C4 C3 C11 N2 -25.5(3) . . . . ?
C2 C3 C11 C13 43.4(4) . . . . ?
C4 C3 C11 C13 -140.3(3) . . . . ?
C2 C3 C11 C12 -82.0(3) . . . . ?
C4 C3 C11 C12 94.3(3) . . . . ?
C11 N2 C14 C5 -30.8(4) . . . . ?
C11 N2 C14 C15 153.0(3) . . . . ?
C6 C5 C14 N2 -179.9(2) . . . . ?
C4 C5 C14 N2 -2.4(4) . . . . ?
C6 C5 C14 C15 -3.6(4) . . . . ?
C4 C5 C14 C15 173.8(2) . . . . ?
C7 C8 C15 C14 0.4(4) . . . . ?
Br1 C8 C15 C14 -179.1(2) . . . . ?
N2 C14 C15 C8 178.6(3) . . . . ?
C5 C14 C15 C8 2.4(4) . . . . ?
loop_
_publcif_info_cif.paper_type
?
