#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:20:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180388 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/57/7205759.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_7205759
loop_
_publ_author_name
'Sarma, Bipul'
'Thakuria, Ranjit'
'Nath, Naba K.'
'Nangia, Ashwini'
_publ_section_title
;
 Crystal structures of mirtazapine molecular salts
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3232
_journal_paper_doi               10.1039/c0ce00746c
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C20 H23 N3 O4'
_chemical_formula_weight         369.41
_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                111.053(2)
_cell_angle_beta                 115.931(2)
_cell_angle_gamma                99.711(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3222(16)
_cell_length_b                   10.7865(17)
_cell_length_c                   10.8589(17)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.20
_cell_volume                     935.2(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0363
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9393
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0565
_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)+(0.0483P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                2957
_reflns_number_total             3686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00746c.txt
_cod_data_source_block           Mrtz-malonate
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7205759
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
C1 C -0.3770(2) 0.6894(2) 0.1307(2) 0.0435(5) Uani 1 1 d . . .
H1 H -0.4583 0.6491 0.1384 0.052 Uiso 1 1 calc R . .
C2 C -0.4131(2) 0.7158(2) 0.0085(2) 0.0480(5) Uani 1 1 d . . .
H2 H -0.5164 0.6913 -0.0672 0.058 Uiso 1 1 calc R . .
C3 C -0.2917(3) 0.7802(2) 0.0001(2) 0.0464(5) Uani 1 1 d . . .
H3 H -0.3129 0.7996 -0.0820 0.056 Uiso 1 1 calc R . .
C4 C -0.1393(2) 0.8157(2) 0.1132(2) 0.0371(4) Uani 1 1 d . . .
C5 C -0.0008(3) 0.8925(2) 0.1179(3) 0.0458(5) Uani 1 1 d . . .
H5A H 0.0728 0.9747 0.2218 0.055 Uiso 1 1 calc R . .
H5B H -0.0343 0.9278 0.0434 0.055 Uiso 1 1 calc R . .
C6 C 0.0790(2) 0.7932(2) 0.0784(2) 0.0410(5) Uani 1 1 d . . .
C7 C 0.0889(3) 0.7617(3) -0.0521(3) 0.0541(6) Uani 1 1 d . . .
H7 H 0.0516 0.8068 -0.1110 0.065 Uiso 1 1 calc R . .
C8 C 0.1527(3) 0.6650(3) -0.0964(3) 0.0614(7) Uani 1 1 d . . .
H8 H 0.1601 0.6465 -0.1830 0.074 Uiso 1 1 calc R . .
C9 C 0.2052(3) 0.5962(2) -0.0114(3) 0.0557(6) Uani 1 1 d . . .
H9 H 0.2471 0.5299 -0.0412 0.067 Uiso 1 1 calc R . .
C10 C 0.1957(2) 0.6254(2) 0.1180(2) 0.0454(5) Uani 1 1 d . . .
H10 H 0.2313 0.5781 0.1746 0.055 Uiso 1 1 calc R . .
C11 C 0.1339(2) 0.72463(19) 0.1659(2) 0.0362(4) Uani 1 1 d . . .
C12 C 0.1436(2) 0.7560(2) 0.3179(2) 0.0350(4) Uani 1 1 d . . .
C13 C 0.3110(2) 0.8567(2) 0.4525(2) 0.0393(5) Uani 1 1 d . . .
H13A H 0.3823 0.8170 0.4336 0.047 Uiso 1 1 calc R . .
H13B H 0.3329 0.9493 0.4561 0.047 Uiso 1 1 calc R . .
C14 C 0.2213(2) 0.9253(2) 0.6314(2) 0.0484(5) Uani 1 1 d . . .
H14A H 0.2388 1.0217 0.6447 0.058 Uiso 1 1 calc R . .
H14B H 0.2342 0.9287 0.7267 0.058 Uiso 1 1 calc R . .
C15 C 0.0573(2) 0.8247(2) 0.4952(2) 0.0450(5) Uani 1 1 d . . .
H15A H 0.0373 0.7290 0.4843 0.054 Uiso 1 1 calc R . .
H15B H -0.0171 0.8585 0.5138 0.054 Uiso 1 1 calc R . .
C16 C -0.1149(2) 0.77890(18) 0.2307(2) 0.0324(4) Uani 1 1 d . . .
C17 C 0.5010(3) 0.9787(3) 0.7367(3) 0.0594(6) Uani 1 1 d . . .
H17A H 0.5187 1.0714 0.7425 0.089 Uiso 1 1 calc R . .
H17B H 0.5733 0.9423 0.7186 0.089 Uiso 1 1 calc R . .
H17C H 0.5159 0.9876 0.8337 0.089 Uiso 1 1 calc R . .
C18 C 0.3240(2) 0.5404(2) 0.5442(2) 0.0430(5) Uani 1 1 d . . .
C19 C 0.3610(3) 0.4281(2) 0.5906(2) 0.0445(5) Uani 1 1 d . . .
H19A H 0.4697 0.4715 0.6765 0.053 Uiso 1 1 calc R . .
H19B H 0.2984 0.4062 0.6311 0.053 Uiso 1 1 calc R . .
C20 C 0.3363(2) 0.2880(2) 0.4676(3) 0.0476(5) Uani 1 1 d . . .
H3A H 0.328(2) 0.791(3) 0.606(2) 0.051(6) Uiso 1 1 d . . .
H4A H 0.290(4) 0.376(4) 0.339(4) 0.105(10) Uiso 1 1 d . . .
N1 N -0.23103(18) 0.71810(16) 0.24031(18) 0.0373(4) Uani 1 1 d . . .
N2 N 0.03853(18) 0.81920(17) 0.35179(18) 0.0365(4) Uani 1 1 d . . .
N3 N 0.33863(19) 0.87757(18) 0.60586(19) 0.0399(4) Uani 1 1 d . . .
O1 O 0.3281(2) 0.64859(17) 0.64299(19) 0.0633(5) Uani 1 1 d . . .
O2 O 0.2953(2) 0.52151(19) 0.4133(2) 0.0689(5) Uani 1 1 d . . .
O3 O 0.3589(2) 0.19244(18) 0.4961(2) 0.0697(5) Uani 1 1 d . . .
O4 O 0.2906(2) 0.2748(2) 0.3295(2) 0.0736(5) Uani 1 1 d . . .
H12 H 0.124(2) 0.668(2) 0.321(2) 0.029(5) Uiso 1 1 d . . .
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
N1 C1 C2 123.69(19) . . ?
C1 C2 C3 118.09(19) . . ?
C4 C3 C2 120.14(19) . . ?
C3 C4 C16 117.29(18) . . ?
C3 C4 C5 123.62(18) . . ?
C16 C4 C5 119.09(18) . . ?
C4 C5 C6 110.93(16) . . ?
C7 C6 C11 119.13(19) . . ?
C7 C6 C5 120.13(19) . . ?
C11 C6 C5 120.60(17) . . ?
C8 C7 C6 121.5(2) . . ?
C9 C8 C7 119.4(2) . . ?
C8 C9 C10 120.0(2) . . ?
C9 C10 C11 121.3(2) . . ?
C10 C11 C6 118.66(18) . . ?
C10 C11 C12 115.68(18) . . ?
C6 C11 C12 125.51(17) . . ?
N2 C12 C11 119.29(16) . . ?
N2 C12 C13 107.60(15) . . ?
C11 C12 C13 107.78(15) . . ?
N3 C13 C12 111.99(16) . . ?
N3 C14 C15 111.26(16) . . ?
N2 C15 C14 109.25(17) . . ?
N1 C16 N2 117.90(16) . . ?
N1 C16 C4 122.89(17) . . ?
N2 C16 C4 118.95(16) . . ?
O2 C18 O1 124.25(19) . . ?
O2 C18 C19 118.77(19) . . ?
O1 C18 C19 116.96(18) . . ?
C20 C19 C18 118.30(18) . . ?
O3 C20 O4 121.7(2) . . ?
O3 C20 C19 121.4(2) . . ?
O4 C20 C19 116.94(19) . . ?
C16 N1 C1 117.82(17) . . ?
C16 N2 C15 115.75(15) . . ?
C16 N2 C12 120.43(15) . . ?
C15 N2 C12 109.17(15) . . ?
C13 N3 C17 111.57(17) . . ?
C13 N3 C14 110.47(15) . . ?
C17 N3 C14 111.79(16) . . ?
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
C1 N1 1.338(2) . ?
C1 C2 1.363(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.378(3) . ?
C4 C16 1.402(3) . ?
C4 C5 1.496(3) . ?
C5 C6 1.511(3) . ?
C6 C7 1.388(3) . ?
C6 C11 1.395(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.373(4) . ?
C9 C10 1.376(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.514(3) . ?
C12 N2 1.482(2) . ?
C12 C13 1.523(3) . ?
C13 N3 1.483(2) . ?
C14 N3 1.486(3) . ?
C14 C15 1.506(3) . ?
C15 N2 1.461(2) . ?
C16 N1 1.331(2) . ?
C16 N2 1.401(2) . ?
C17 N3 1.485(3) . ?
C18 O2 1.247(2) . ?
C18 O1 1.248(3) . ?
C18 C19 1.514(3) . ?
C19 C20 1.501(3) . ?
C20 O3 1.208(3) . ?
C20 O4 1.303(3) . ?
