An unprecedented case of dodecamorphism: the twelfth polymorph of aripiprazole formed by seeding with its active metabolite
Zeidan, T. A.; Trotta, J. T.; Tilak, P. A.; Oliveira, M. A.; Chiarella, R. A.; Foxman, B. M.; Almarsson, Ö.; Hickey, M. B.; CrystEngComm 18 (2016) 1486–; doi:10.1039/C5CE02467F

data_7223876
_publ_section_title
;
 An unprecedented case of dodecamorphism: the twelfth polymorph of
 aripiprazole formed by seeding with its active metabolite
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1486
_journal_paper_doi               10.1039/C5CE02467F
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2'
_chemical_formula_sum            'C23 H27 Cl2 N3 O2'
_chemical_formula_weight         448.39
_chemical_melting_point          400
_chemical_name_common
'aripiprazole; 7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydrocarbostyril'
_chemical_name_systematic
7-(4-(4-(2,3-Dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydro-2(1H)-quinolinone
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-20
_audit_creation_method           CRYSTALS_ver_14.52
_audit_update_record
;
2015-09-03 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.9900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6133(10)
_cell_length_b                   6.9533(4)
_cell_length_c                   19.4632(11)
_cell_measurement_reflns_used    7392
_cell_measurement_temperature    173
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     2150.2(2)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17022
_diffrn_reflns_theta_full        25.387
_diffrn_reflns_theta_max         25.387
_diffrn_reflns_theta_min         1.913
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1-propanol'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9636
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.0006796
_refine_ls_shift/su_mean         0.0000401
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.20P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0824
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0824
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3118
_reflns_number_total             3931
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0462
_oxford_refine_ls_scale          1.001(3)
_oxford_reflns_number_all        3931
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'alxs0101 P 21/n R = 0.04'
_iucr_refine_instructions_details_constraints
;
BLOCK 
CONT SCALE 
CONT CL   (    1 ,X'S,U'S)  UNTIL N    (   24 ) 
CONT C    (    2 ,X'S,U'S) 
CONT C    (    3 ,X'S,U'S) 
CONT C    (    5 ,X'S,U'S) 
CONT C    (    6 ,X'S,U'S) 
CONT C    (    7 ,X'S,U'S)  UNTIL C    (   10 ) 
CONT C    (   11 ,X'S,U'S) 
CONT C    (   12 ,X'S,U'S) 
CONT C    (   13 ,X'S,U'S) 
CONT C    (   14 ,X'S,U'S) 
CONT C    (   15 ,X'S,U'S) 
CONT C    (   16 ,X'S,U'S) 
CONT C    (   18 ,X'S,U'S)  UNTIL C    (   19 ) 
CONT C    (   20 ,X'S,U'S)  UNTIL C    (   22 ) 
CONT C    (   23 ,X'S,U'S) 
CONT C    (   25 ,X'S,U'S)  UNTIL C    (  271 ) 
CONT C    (  260 ,X'S,U[ISO])  UNTIL C    (  261 ) 
EQUIVALENCE PART(1001, OCC) 
CONTINUE    PART(1002, OCC) 
WEIGHT -1   PART(1002, OCC) 
RIDE N   (  24,X'S) H   ( 241,X'S) 
RIDE C   (   2,X'S) H   (  22,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  32,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   ( 270,X'S) H   (2701,X'S) H   (2702,X'S) 
RIDE C   ( 271,X'S) H   (2711,X'S) H   (2712,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c5ce02467f2.cif
_cod_data_source_block           alxs101
_cod_depositor_comments
'Adding full bibliography for 7223876--7223877.cif.'
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               7223876